2- 4-biphenyloxymethylene!anilides, preparation thereof and intermediates therefor, and use thereof

ABSTRACT

2- 4-Biphenyloxymethylene!anilides of the formula I ##STR1## where the indices and the substituents have the following meanings: R, R 1  and R 2  are cyano, nitro, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkylcarbonyl(alkylamino), alkenyl, alkenyloxy, alkynyl, alkynyloxy, cycloalkyl or C(R a )═NOR b  ; 
     R a  and R b  are hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl; 
     m is 1, 2, 3, 4 or 5; 
     n is 0, 1 or 2; 
     R 3  is nitro, cyano, halogen, 
     n is 0, 1 or 2, 
     unsubst. or subst. alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy or 
     alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkylcarbonyl(alkylamino), C(R a )═NOR b  or 
     o is 0, 1, 2, 3 or 4; 
     R 4  is hydrogen, 
     unsubst. or subst. alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkylcarbonyl or alkoxycarbonyl; 
     X is a direct bond or CH 2 , O or NR c  ; 
     R c  is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl; 
     R 5  is alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, or 
     or in the case where X is NR c , is additionally hydrogen, 
     processes and intermediates for their preparation, and their use are described.

The present invention relates to 2- 4-biphenyloxymethylene !-anilides ofthe formula I ##STR2## where the indices and the substituents have thefollowing meanings: R is cyano, nitro, halogen, C₁ -C₄ -alkyl, C₁ -C₄-haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁-C₄ -halo-alkylthio, C₁ -C₄ -alkylamino, di-C₁ -C₄ -alkylamino, C₁ -C₄-alkyl-carbonyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylaminocarbonyl,di(C₁ -C₄ -alkyl)aminocarbonyl, C₁ -C₄ -alkylcarbonylamino, C₁ -C₄-alkylcarbonyl(C₁ -C₄ -alkylamino), C₂ -C₄ -alkenyl, C₃ -C₄ -alkenyloxy,C₂ -C₄ -alkynyl, C₃ -C₄ -alkynyloxy, C₃ -C₆ -cyclo-alkyl orC(R^(a))═NOR^(b) ;

R^(a) and R^(b) are hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl orcycloalkenyl;

m is 1, 2, 3, 4 or 5, it being possible for the radicals R to bedifferent if m is greater than 1;

R¹ is cyano, nitro, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄-alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -halo-alkylthio,C₁ -C₄ -alkylamino, di-C₁ -C₄ -alkylamino, C₁ -C₄ -alkyl-carbonyl, C₁-C₄ -alkoxycarbonyl, C₁ -C₄ -alkylaminocarbonyl, di(C₁ -C₄-alkyl)aminocarbonyl, C₁ -C₄ -alkylcarbonylamino, C₁ -C₄-alkylcarbonyl(C₁ -C₄ -alkylamino), C₂ -C₄ -alkenyl, C₃ -C₄ -alkenyloxy,C₂ -C₄ -alkynyl, C₃ -C₄ -alkynyloxy, C₃ -C₆ -cyclo-alkyl orC(R^(a))═NOR^(b) ;

n is 0, 1 or 2, it being possible for the radicals R¹ to be different ifn is 2;

R² is cyano, nitro, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄-alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -halo- alkylthio,C₁ -C₄ -alkylamino, di-C₁ -C₄ -alkylamino, C₁ -C₄ -alkyl-carbonyl, C₁-C₄ -alkoxycarbonyl, C₁ -C₄ -alkylaminocarbonyl, di(C₁ -C₄-alkyl)aminocarbonyl, C₁ -C₄ -alkylcarbonylamino, C₁ -C₄-alkylcarbonyl(C₁ -C₄ -alkylamino), C₂ -C₄ -alkenyl, C₃ -C₄ -alkenyloxy,C₂ -C₄ -alkynyl, C₃ -C₄ -alkynyloxy, C₃ -C₆ -cyclo-alkyl orC(R^(a))═NOR^(b) ;

R³ is nitro, cyano, halogen,

unsubst. or subst. alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy,alkynyloxy or

C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄-alkylamino-carbonyl, di(C₁ -C₄ -alkyl)aminocarbonyl, C₁ -C₄-alkylcarbonyl-amino, C₁ -C₄ -alkylcarbonyl(C₁ -C₄ -alkylamino),C(R^(a))═NOR^(b) or

in the case where o is greater than 1, is additionally an unsubst. orsubst. bridge bonded to two adjacent ring atoms, which can carry threeto four members from the group consisting of 3 or 4 carbon atoms, and 2or 3 carbon atoms and 1 or 2 nitrogen, oxygen and/or sulfur atoms, itbeing possible for this bridge, together with the ring to which it isbonded, to form a partially unsaturated or aromatic radical;

o is 0, 1, 2, 3 or 4, it being possible for the substituents R³ to bedifferent if n is greater than 1;

R⁴ is hydrogen,

unsubst. or subst. alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl,alkylcarbonyl or alkoxycarbonyl;

X is a direct bond or CH₂, O or NR^(c) ;

R^(c) is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl;

R⁵ is alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, or or in thecase where X is NR^(c), is additionally hydrogen.

In addition, the invention relates to processes and intermediates forpreparing these compounds, compositions containing them and their usefor controlling animal pests or harmful fungi. WO-A 3/15,046 describes2- 4-biphenyloxymethylene!anilides in general form for controllinganimal pests and harmful fungi, the active compounds of this groupdescribed there carrying substituents either on one or the other phenylring of the biphenyl system. However, these compounds leave something tobe desired in practice with respect to the control success or theapplication rates required.

It is an object of the present invention to provide compounds havingimproved properties.

We have found that this object is achieved by the compounds I defined atthe outset. Processes and intermediates for their preparation,compositions containing them and their use for controlling animal pestsor harmful fungi have additionally been found.

The compounds I are obtainable in various ways.

Those compounds I where R⁴ is hydrogen and X is a direct bond or oxygenare obtained, for example, by converting a benzyl derivative of theformula II into the corresponding 2- 4-biphenyloxymethylene!nitrobenzeneof the formula IV in the presence of a base using a 4-biphenol of theformula III, then reducing IV to the N-hydroxylaniline of the formula Vaand converting Va into I using a carbonyl compound of the formula VI.##STR3## L¹ in the formula II and L² in the formula VI are each anucleophilically replaceable group, for example halogen (eg. chlorine,bromine or iodine), or an alkyl- or arylsulfonate (eg. methanesulfonate,trifluoromethanesulfonate, benzenesulfonate or 4-toluenesulfonate).

The etherification of the compounds II and III is customarily carriedout at from 0° C. to 80° C., preferably 20° C. to 60° C.

Suitable solvents are aromatic hydrocarbons such as toluene, o-,m- andp-xylene, halogenated hydrocarbons such as methylene chloride,chloroform and chlorobenzene, ethers such as diethyl ether, diisopropylether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran,nitriles such as acetonitrile and propionitrile, alcohols such asmethanol, ethanol, n-propanol, i-propanol, n-butanol and tert-butanol,ketones such as acetone and methylethyl ketone and also dimethylsulfoxide, dimethyl-formamide, dimethylacetamide,1,3-dimethylimidazolidin-2-one and1,2-dimethyltetrahydro-2(1H)-pyrimidine, preferably methylene chloride,acetone and dimethylformamide. Mixtures of the solvents mentioned canalso be used.

Suitable bases are generally inorganic compounds such as alkali metaland alkaline earth metal hydroxides (eg. lithium hydroxide, sodiumhydroxide, potassium hydroxide and calcium hydroxide), alkali metal andalkaline earth metal oxides (eg. lithium oxide, sodium oxide, calciumoxide and magnesium oxide), alkali metal and alkaline earth metalhydrides (eg. lithium hydride, sodium hydride, potassium hydride andcalcium hydride), alkali metal amides (eg. lithium amide, sodium amideand potassium amide), alkali metal and alkaline earth metal carbonates(eg. lithium carbonate and calcium carbonate) and also alkali metalhydrogen-carbonates (eg. sodium hydrogencarbonate), organometalliccompounds, in particular alkali metal alkyls (eg. methyllithium,butyllithium and phenyllithium), alkylmagnesium halides (eg.methylmagnesium chloride) and also alkali metal and alkaline earth metalalkoxides (eg. sodium methoxide, sodium ethoxide, potassium ethoxide,potassium tert-butoxide and dimethoxymagnesium), additionally organicbases, eg. tertiary amines such as trimethylamine, triethylamine,triisopropylethylamine and N-methylpiperidine, pyridine, substitutedpyridines such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Sodium hydroxide, potassium carbonate andpotassium tert-butoxide are particularly preferred.

The bases are in general used in an equimolar amount, in an excess or,if desired, as a solvent.

It may be advantageous for the reaction to add a catalytic amount of acrown ether (eg. 18-crown-6 or 15-crown-5).

The reaction can also be carried out in two-phase systems consisting ofa solution of alkali metal or alkaline earth metal hydroxides orcarbonates in water and an organic phase (eg. aromatic and/orhalogenated hydrocarbons). Suitable phase-transfer catalysts here are,for example, ammonium halides and tetrafluoroborates (eg.benzyltriethylammonium chloride, benzyltributylammonium bromide,tetrabutylammonium chloride, hexadecyltrimethylammonium bromide ortetrabutylammonium tetrafluoroborate) and also phosphonium halides (eg.tetrabutylphosphonium chloride and tetraphenylphosphonium bromide).

It may be advantageous for the reaction first to react the4-hydroxybiphenyl III with the base to give the correspondinghydroxylate, which is then reacted with the benzyl derivative.

The starting substances II required for preparing the compounds I aredisclosed in EP-A 513 580 and WO-A 93/15,046 or can be prepared by themethods described there.

4-Biphenols of the formula III are also known or can be obtained byknown processes cf. Synthesis 1993, 735; Synthesis 1992, 803; Synthesis1992, 413; Pure and Appl. Chem. 66 (1994), 213; J. Org. Chem. 58 (1993),2201; Tetrahedron 44 (1992), 9577; Chem. Rev. 93 (1993), 2117; Acc.Chem. Res. 15 (1982), 340; Pure and Appl. Chem. 52 (1980), 669 !.

The reduction of the nitro compounds IV to the correspondingN-hydroxyanilines Va is carried out in a similar manner to methods knownfrom the literature, for example using metals such as zinc cf. Ann.Chem. 316 (1901), 278! or using hydrogen (cf. EP-A 085 890).

The reaction of the N-hydroxyanilines Va with the carbonyl compounds VIis carried out under alkaline conditions conforming to the conditionsdescribed above for the reaction of the compounds II with the4-biphenols III. The reaction is particularly preferably carried out atfrom -10° C. to 30° C. The preferred solvents are methylene chloride,toluene, tert-butyl methyl ether or ethyl acetate. The preferred basesare sodium hydrogencarbonate, potassium carbonate or aqueous sodiumhydroxide solution.

The compounds of the formula I where X is a direct bond or oxygen areadditionally obtained, for example, by reducing a benzyl derivative ofthe formula IIa first to the corresponding N-hydroxyaniline of theformula Vb, converting Vb into the corresponding anilide of the formulaVII using a carbonyl compound of the formula VI, then converting VIIinto the amide of the formula IX using a compound VIII, then convertingIX into the benzyl halide X and converting X into I in the presence of abase using a 4-biphenol of the formula III. ##STR4##

In the formula X, Hal is a halogen atom, in particular chlorine orbromine.

L³ in the formula VIII is a nucleophilically replaceable group, forexample halogen (eg.: chlorine, bromine or iodine), or an alkyl- orarylsulfonate (eg. methanesulfonate, trifluoro-methanesulfonate,benzenesulfonate or 4-toluenesulfonate) and R⁴ is not hydrogen.

The reactions are carried out analogously to the processes explainedabove.

The halogenation of the compounds IX is carried out using free radicals,it being possible to employ as halogenating agents, for example,N-chloro- or N-bromosuccinimide, elemental halogens (eg. chlorine orbromine) or thionyl chloride, phosphorus trichloride or phosphoruspentachloride and similar compounds. Customarily, a free-radicalinitiator (eg. azobisisobutyronitrile) is additionally used or thereaction is carried out under irradiation (with UV light). Thehalogenation is carried out in a manner known per se in a customaryorganic diluent.

The compounds I where R⁴ is not hydrogen are additionally obtained byreacting a corresponding compound of the formula I where R⁴ is hydrogenwith a compound of the formula VIII. ##STR5##

The reaction is carried out in a manner known per se in an inert organicsolvent in the presence of a base at from 0° C. to 50° C.

The bases used are, in particular, sodium hydrogencarbonate, potassiumcarbonate, sodium hydroxide and aqueous sodium hydroxide solutions.

The solvents used are, in particular, acetone, dimethylformamide,toluene, tert-butyl methyl ether, ethyl acetate and methanol.

The compounds of the formula I where X is NR^(c) are advantageouslyobtained by converting a benzanilide of the formula IXa into thecorresponding benzyl halide of the formula Xa, converting Xa into acompound of the formula I.A in the presence of a base using a 4-biphenolof the formula III and then reacting I.A with an amine of the formula XIto give I. ##STR6##

A in the formula IXa is alkyl (in particular C₁ -C₆ -alkyl) or phenyl;Hal in the formula Xa is halogen (in particular chlorine or bromine).

The reactions of IXa to Xa and of Xa to I.A are carried out in generaland in particular under the conditions described above.

The reaction of the compounds I.A with the primary or secondary aminesof the formula XIa or XIb is carried out at from 0° C. to 100° C. in aninert solvent or in a solvent mixture.

Suitable solvents are, in particular, water, tert-butyl methyl ether andtoluene or mixtures thereof. It may be advantageous for improving thesolubility of the starting materials additionally to add one of thefollowing solvents (as solubilizer): tetrahydrofuran, methanol,dimethylformamide or ethylene glycol ether.

The amines XIa and XIb are customarily employed in an excess of up to100% based on the compounds X or can be used as solvents. It may beadvantageous with respect to the yield to carry out the reaction underpressure.

Amides of the formula I.A (A=phenyl) are obtained by reaction of thehydroxyanilines V.A with an acylating agent VI.A (A=phenyl).

The compound I.A can be reacted with an amine of the formula XIa or XIbto give the compound I (R⁴ =H, X=NR^(c)). Reaction of the compound I (R⁴=H, X=NR^(c)) with an electrophile VIII gives the compounds I (R⁴ ≠H,X=NR^(c)). ##STR7##

In addition, the compounds I are also obtained, for example, by reactinga compound XIV with an organometallic compound XV in the presence of apalladium catalyst. ##STR8##

Hal in the formula XIV is a halogen atom (for example chlorine, bromineor iodine).

L-M in the formula XV is an organometallic radical such as a magnesiumhalide, or B(OH)₂ or trialkyltin.

The reaction conditions of the biphenyl synthesis correspond to thebiphenyl syntheses known according to the literature cf. Synthesis 1993,735; Synthesis 1992, 803; Synthesis 1992, 413; Pure and Appl. Chem. 66(1994), 213; J. Org. Chem. 58 (1993), 2201; Tetrahedron 44 (1992), 9577;Chem. Rev. 93 (1993), 2117; Acc. Chem. Res. 15 (1982), 340; Pure andAppl. Chem. 52 (1980), 669 !.

The compounds I are prepared analogously to the methods described inWO-A 93/15,046 via intermediates of the formula XII ##STR9## where Y isNO₂, NHOH, NHOR⁴, N(OH)-CO₂ C₆ H₅ or N(OR⁴)-CO₂ C₆ H₅ and the indices m,n and o and the substituents R, R¹, R², R³ and R⁴ have the meaningsgiven in claim 1.

Additionally, the compounds I can be prepared via intermediates of theformula XII.A ##STR10## according to the methods of biaryl synthesis(for literature references see above),

where W is NO₂,NHOH, NHOR⁴, N(OR⁴)COXR⁵ or N(oR⁴)CO₂ phenyl, L⁴ ishalogen (C1 , Br, I) or O-SO₂ -CF₃ or an organometallic group,corresponding to the methods of the abovementioned biaryl syntheses and

R¹ _(n), R², R³ _(o), R⁴, R⁵ and X have the meanings mentioned in claim1.

The compounds I can contain acidic or basic centers and accordingly formacid addition products or base addition products or salts.

Acids for acid addition products are, inter alia, mineral acids (eg.halohydric acids such as hydrochloric and hydrobromic acids, phosphoricacid, sulfuric acid, nitric acid), organic acids (eg. formic acid,acetic acid, oxalic acid, malonic acid, lactic acid, malic acid,succinic acid, tartaric acid, citric acid, salicylic acid,p-toluenesulfonic acid, dodecylbenzenesulfonic acid) or otherproton-acidic compounds (eg. saccharin). Bases for base additionproducts are, inter alia, oxides, hydroxides, carbonates orhydrogencarbonates of alkali metals or alkaline earth metals (eg.potassium or sodium hydroxide or carbonate) or ammonium compounds (eg.ammonium hydroxide).

In the definitions of the symbols indicated in the above formulae, insome cases collective terms were used which are generally representativeof the following substituents:

halogen: fluorine, chlorine, bromine and iodine;

alkyl: saturated, straight-chain or branched hydrocarbon radicals having1 to 4 or 10 carbon atoms, eg. methyl, ethyl, propyl, 1-methylethyl,butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;

haloalkyl: straight-chain or branched alkyl groups having 1 to 4 carbonatoms (as mentioned above), it being possible in these groups for thehydrogen atoms to be replaced partially or completely by halogen atomsas mentioned above, eg. C₁ -C₂ -haloalkyl such as chloromethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,2,2,2-trichloroethyl and pentafluoroethyl;

alkylcarbonyl: straight-chain or branched alkyl groups in particularhaving 1 to 10 carbon atoms (as mentioned above), which are bonded tothe structure via a carbonyl group (-CO-);

alkoxy: straight-chain or branched alkyl groups, having 1 to 4 or 10carbon atoms (as mentioned above), which are bonded to the structure viaan oxygen atom (-O-);

alkoxycarbonyl: straight-chain or branched alkoxy groups, having 1 to 4carbon atoms (as mentioned above), which are bonded to the structure viaa carbonyl group (-CO-);

alkylthio: straight-chain or branched alkyl groups, having 1 to 4 carbonatoms (as mentioned above), which are bonded to the structure via asulfur atom (-S-);

unsubst. or subst. alkyl: saturated, straight-chain or branchedhydrocarbon radicals, in particular having 1 to 10 carbon atoms, eg. C₁-C₆ -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl,1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

unsubst. or subst. alkenyl: unsaturated, straight-chain or branchedhydrocarbon radicals, in particular having 2 to 10 carbon atoms and adouble bond in any desired position, eg. C₂ -C₆ -alkenyl such asethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl,3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

unsubst. or subst. alkenyloxy: straight-chain or branched alkenylgroups, having 3 to 10 carbon atoms (as mentioned above), which arebonded to the structure via an oxygen atom (-O-);

alkynyl: straight-chain or branched hydrocarbon groups, in particularhaving 2 to 20 carbon atoms and a triple bond in any desired position,eg. C₂ -C₆ -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl,2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl,3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl,1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl,5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl,3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl,4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl,1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and1-ethyl-1-methyl-2-propynyl;

unsubst. or subst. alkynyloxy: straight-chain or branched alkynyl groupshaving 3 to 10 carbon atoms (as mentioned above), which are bonded tothe structure via an oxygen atom (-O-);

unsubst. or subst. cycloalkyl: mono- or bicyclic hydrocarbon radicalshaving 3 to 10 carbon atoms, eg. C₃ -C₁₀ -(bi)cycloalkyl such ascyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, bornanyl,norbornanyl, dicyclohexyl, bicyclo 3.3.0!octyl, bicyclo 3.2.1!octyl,bicyclo 2.2.2!octyl or bicyclo 3.3.1!nonyl;

unsubst. or subst. cycloalkenyl: mono- or bicyclic hydrocarbon radicalshaving 5 to 10 carbon atoms and a double bond in any desired ringposition, eg. C₅ -C₁₀ -(bi)cycloalkenyl such as cyclopentenyl,cyclohexenyl, cycloheptenyl, bornenyl, norbornenyl, dicyclohexenyl andbicyclo 3.3.0!octenyl;

an unsubst. or subst. bridge bonded to two adjacent ring atoms, whichcan carry three or four members from the group consisting of 3 or 4carbon atoms, and 1 to 3 carbon atoms and 1 or 2 nitrogen, oxygen and/orsulfur atoms, it being possible for this bridge, together with the ringto which it is bonded, to form a partially unsaturated or aromaticradical: bridges which, with the ring to which they are bonded, form,for example, one of the following systems: quinolinyl, benzofuranyl andnaphthyl;

an unsubst. or subst. saturated or mono- or diunsaturated ring which, inaddition to carbon atoms, can contain one to three of the followingheteroatoms as ring members: oxygen, sulfur and nitrogen, for examplecarbocycles such as cyclopropyl, cyclopentyl, cyclohexyl,cyclopent-2-enyl, cyclohex-2-enyl, 5- to 6-membered, saturated orunsaturated heterocycles, containing one to three nitrogen atoms and/oran oxygen or sulfur atom, such as 2-tetrahydrofuranyl,3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl,2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl,5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl,2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl,4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl,2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl,2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl,2,4-dihydrothien-3-yl, 2,3-pyrrolin-2-yl, 2,3-pyrrolin-3-yl,2,4-pyrrolin-2-yl, 2,4-pyrrolin-3-yl, 2,3-isoxazolin-3-yl,3,4-isoxazolin-3-yl, 4,5-isoxazolin-3-yl, 2,3-isoxazolin-4-yl,3,4-isoxazolin-4-yl, 4,5-isoxazolin-4-yl, 2,3-isoxazolin-5-yl,3,4-isoxazolin-5-yl, 4,5-isoxazolin-5-yl, 2,3-isothiazolin-3-yl,3,4-isothiazolin-3-yl, 4,5-isothiazolin-3-yl, 2,3-isothiazolin-4-yl,3,4-isothiazolin-4-yl, 4,5-isothiazolin-4-yl, 2,3-isothiazolin-5-yl,3,4-isothiazolin-5-yl, 4,5-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl,2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl,2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl,3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl,3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl,4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl,4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl,2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl,2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl,3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl,3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl,4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-tetrahydropyridazinyl,4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl,4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl,1,3,5-tetrahydrotriazin-2-yl and 1,2,4-tetrahydrotriazin-3-yl,preferably 2-tetrahydrofuranyl, 2-tetrahydrothienyl, 2-pyrrolidinyl,3-isoxazolidinyl, 3-isothiazolidinyl, 1,3,4-oxazolidin-2-yl,2,3-dihydrothien-2-yl, 4,5-isoxazolin-3-yl, 3-piperidinyl,1,3-dioxan-5-yl, 4-piperidinyl, 2-tetrahydropyranyl, 4-tetrahydropyranyland morpholinyl;

or an unsubst. or subst. mono- or dinuclear aromatic ring system which,in addition to carbon atoms, can contain one to four 30 nitrogen atoms,or one or two nitrogen atoms and an oxygen or sulfur atom, or an oxygenor sulfur atom, as ring members, ie. aryl radicals such as phenyl andnaphthyl, preferably phenyl or 1- or 2-naphthyl, and hetaryl radicals,for example 5-membered ring heteroaromatics containing one to threenitrogen atoms and/or an oxygen or sulfur atom, such as 2-furyl,3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl,3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,4-isothiazolyl, 5-isothiazolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl,5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl,4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl,1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl, 1,2,5-triazol-3-yl, 1,2,3-triazol-4-yl,1,2,3-triazol-5-yl, 1,2,3-triazol-4-yl, 5-tetrazolyl,1,2,3,4-thiatriazol-5-yl and 1,2,3,4-oxatriazol-5-yl, in particular3-isoxazolyl, 5-isoxazolyl, 4-oxazolyl, 4-thiazolyl,1,3,4-oxadiazol-2-yl and 1,3,4-thiadiazol-2-yl;

six-membered ring heteroaromatics containing one to four nitrogen atomsand heteroatoms, such as 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and1,2,4,5-tetrazin-3-yl, in particular 2-pyridinyl, 3-pyridinyl,4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 2-pyrazinyl and4-pyridazinyl.

The addition of unsubst. or subst. in relation to alkyl, alkenyl andalkynyl groups is intended to express that these groups can be partiallyor completely halogenated (ie. the hydrogen atoms of these groups can bepartially or completely replaced by identical or different halogen atomsas mentioned above (preferably fluorine, chlorine and bromine, inparticular fluorine and chlorine) and/or can carry one to three, inparticular one, of the following radicals:

C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkylthio, C₁ -C₆-haloalkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆ -alkylamino, C₂ -C₆-alkenyloxy, C₂ -C₆ -haloalkenyloxy, C₂ -C₆ -alkynyloxy, C₂ -C₆-haloalkynyloxy, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyloxy, C₃ -C₆-cycloalkenyl, C₃ -C₆ -cycloalkenyloxy,

or an unsubst. or subst. mono- or binuclear aromatic ring system which,in addition to carbon atoms, can contain one to four nitrogen atoms orone or two nitrogen atoms and an oxygen or sulfur atom or an oxygen orsulfur atom as ring members (as mentioned above), which can be bonded tothe substituents directly or via an oxygen atom (-O-), a sulfur atom(-S-) or an amino group (-NR^(a) -), ie. aryl radicals such as phenyland naphthyl, preferably phenyl or 1- or 2-naphthyl, and hetarylradicals, for example 5-membered ring heteroaromatics containing one tothree nitrogen atoms and/or an oxygen or sulfur atom such as 2-furyl,3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl,3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,4-isothiazolyl, 5-isothiazolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl,5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl,4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl,1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl, 1,2,5-triazol-3-yl, 1,2,3-triazol-4-yl,1,2,3-triazol-5-yl, 1,2,3-triazol-4-yl, 5-tetrazolyl,1,2,3,4-thiatriazol-5-yl and 1,2,3,4-oxatriazol-5-yl, in particular3-isoxazolyl, 5-isoxazolyl, 4-oxazolyl, 4-thiazolyl,1,3,4-oxadiazol-2-yl and 1,3,4-thiadiazol-2-yl;

six-membered ring heteroaromatics containing one to four nitrogen atomsas heteroatoms, such as 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and1,2,4,5-tetrazin-3-yl, in particular 2-pyridinyl, 3-pyridinyl,4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 2-pyrazinyl and4-pyridazinyl.

The addition of unsubst. or subst. in relation to the cyclic (saturated,unsaturated or aromatic) groups is intended to express that these groupscan be partially or completely halogenated (ie. the hydrogen atoms ofthese groups can be partially or completely replaced by identical ordifferent halogen atoms such as mentioned above (preferably fluorine,chlorine and bromine, in particular fluorine and chlorine) and/or cancarry one to three of the following radicals:

nitro;

cyano, thiocyanato;

alkyl, particularly C₁ -C₆ -alkyl as mentioned above, preferably methyl,ethyl, 1-methylethyl, 1,1-dimethylethyl, butyl, hexyl, in particularmethyl and 1-methylethyl;

C₁ -C₄ -haloalkyl, as mentioned above, preferably trichloromethyl,difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyland pentafluoroethyl;

C₁ -C₄ -alkoxy, preferably methoxy, ethoxy, 1-methylethoxy and1,1-dimethylethoxy, in particular methoxy;

C₁ -C₄ -haloalkoxy, particularly C₁ -C₂ -haloalkoxy, preferablydifluoromethoxy, trifluoromethoxy and 2,2,2-trifluoroethoxy, inparticular difluoromethoxy;

C₁ -C₄ -alkylthio, preferably methylthio and 1-methylethylthio, inparticular methylthio;

C₁ -C₄ -alkylamino such as methylamino, ethylamino, propylamino,1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylaminoand 1,1-dimethylethylamino, preferably methylamino and1,1-dimethylethylamino, in particular methylamino,

di-C₁ -C₄ -alkylamino such as N,N-dimethylamino, N,N-diethylamino,N,N-dipropylamino, N,N-di(1-methylethyl)amino, N,N-dibutylamino,N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino,N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino,N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino,N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino,N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino,N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino,N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino,N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino,N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino,N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino,N-(1 -methylethyl)- N-(1-methylpropyl)amino,N-(1-methylethyl)-N-(2-methylpropyl)-amino,N-(1,1-dimethylethyl)-N-(l-methylethyl)amino,N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino,N-butyl-N-(1,1-dimethylethyl)amino,N-(l-methylpropyl)-N-(2-methylpropyl)amino,N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino andN-(1,1-dimethylethyl)-N-(2-methylpropyl)amino, preferablyN,N-dimethylamino and N,N-diethylamino, in particular N,N-dimethylamino;

C₁ -C₆ -alkylcarbonyl such as methylcarbonyl, ethylcarbonyl,propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl,1-methylpropylcarbonyl, 2-methylpropylcarbonyl,1,1-dimethylethylcarbonyl, pentylcarbonyl, 1-methylbutylcarbonyl,2-methylbutylcarbonyl, 3-methylbutylcarbonyl,1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl,2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl,1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl,4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl,1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl,2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl,3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl,1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl,1-ethyl-1-methylpropylcarbonyl and 1-ethyl-2-methylpropylcarbonyl,preferably methylcarbonyl, ethylcarbonyl and 1,1-dimethylcarbonyl, inparticular ethylcarbonyl;

C₁ -C₆ -alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, 5propyloxycarbonyl, 1-methylethoxycarbonyl, butyloxycarbonyl,1-methylpropyloxycarbonyl, 2-methylpropyloxycarbonyl,1,1-dimethylethoxycarbonyl, pentyloxycarbonyl, 1-methylbutyloxycarbonyl,2-methylbutyloxycarbonyl, 3-methylbutyloxycarbonyl,2,2-dimethylpropyloxycarbonyl, 1-ethylpropyloxycarbonyl,hexyloxycarbonyl, 1,1-dimethylpropoxycarbonyl,1,2-dimethylpropyloxycarbonyl, 1-methylpentyloxycarbonyl,2-methylpentyloxycarbonyl, 3-methylpentyloxycarbonyl,4-methylpentyloxycarbonyl, 1,1-dimethylbutyloxycarbonyl,1,2-dimethylbutyloxycarbonyl, 1,3-dimethylbutyloxycarbonyl,2,2-dimethylbutyloxycarbonyl, 2,3-dimethylbutyloxycarbonyl,3,3-dimethylbutyloxycarbonyl, 1-ethylbutyloxycarbonyl,2-ethylbutyloxycarbonyl, 1,1,2-trimethylpropyloxycarbonyl,1,2,2-trimethylpropyloxycarbonyl, 1-ethyl-1-methylpropyloxycarbonyl and1-ethyl-2-methylpropyloxycarbonyl, preferably methoxycarbonyl,ethoxycarbonyl and 1,1-dimethylethoxycarbonyl, in particularethoxycarbonyl;

C₁ -C₆ -alkylaminocarbonyl such as methylaminocarbonyl,ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl,butylaminocarbonyl, 1-methylpropylaminocarbonyl,2-methylpropylaminocarbonyl, 1,1-dimethylethylaminocarbonyl,pentylaminocarbonyl, 1-methylbutylaminocarbonyl,2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl,2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl,hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl,1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl,2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl,4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl,1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl,2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl,3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl,2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl,1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyland 1-ethyl-2-methylpropylaminocarbonyl, preferably methylaminocarbonyland ethylaminocarbonyl, in particular methylaminocarbonyl;

di-C₁ -C₆ -alkylaminocarbonyl, particularly di-C₁ -C₄-alkylaminocarbonyl such as N,N-dimethylaminocarbonyl,N,N-diethylaminocarbonyl, N,N-dipropylaminocarbonyl,N,N-di(1-methylethyl)aminocarbonyl, N,N-dibutylaminocarbonyl,N,N-di(1-methylpropyl)aminocarbonyl,N,N-di(2-methylpropyl)aminocarbonyl,N,N-di(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl,N-methyl-N-propylaminocarbonyl, N-methyl-N-(1-methylethyl)aminocarbonyl,N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl,N-methyl-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-methylaminocarbonyl,N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1methylethyl)aminocarbonyl,N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl,N-ethyl-N-(2-methylpropyl)aminocarbonyl,N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl,N-(1-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl,N-(1-methylpropyl)-N-propylaminocarbonyl,N-(2-methylpropyl)-N-propylaminocarbonyl,N-(1,1-dimethylethyl)-N-propylaminocarbonyl,N-butyl-N-(1-methylethyl)aminocarbonyl,N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl,N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl,N-butyl-N-(1-methylpropyl)aminocarbonyl,N-butyl-N-(2-methylpropyl)aminocarbonyl,N-butyl-N-(1,1-dimethylethyl)aminocarbonyl,N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl andN-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl, preferablyN,N-dimethylaminocarbonyl and N,N-diethylaminocarbonyl, in particularN,N-dimethylaminocarbonyl;

C₁ -C₆ -alkylcarboxyl such as -methylcarboxyl, ethylcarboxyl,propylcarboxyl, 1-methylethylcarboxyl, butylcarboxyl,1-methylpropylcarboxyl, 2-methylpropylcarboxyl,1,1-dimethylethylcarboxyl, pentylcarboxyl, 1-methylbutylcarboxyl,2-methylbutylcarboxyl, 3-methylbutylcarboxyl,1,1-dimethylpropylcarboxyl, 1,2-dimethylpropylcarboxyl,2,2-dimethylpropylcarboxyl, 1-ethylpropylcarboxyl, hexylcarboxyl,1-methylpentylcarboxyl, 2-methylpentylcarboxyl, 3-methylpentylcarboxyl,4-methylpentylcarboxyl, 1,1-dimethylbutylcarboxyl,1,2-dimethylbutylcarboxyl, 1,3-dimethylbutylcarboxyl,2,2-dimethylbutylcarboxyl, 2,3-dimethylbutylcarboxyl,3,3-dimethylbutylcarboxyl, 1-ethylbutylcarboxyl, 2-ethylbutylcarboxyl,1,1,2-trimethylpropylcarboxyl, 1,2,2-trimethylpropylcarboxyl,1-ethyl(1-methylpropylcarboxyl and 1-ethyl-2-methylpropylcarboxyl,preferably methylcarboxyl, ethylcarboxyl and 1,1-dimethylethylcarbonyl,in particular methylcarboxyl and 1,1-dimethylethylcarboxyl;

C₁ -C₆ -alkylcarbonylamino such as methylcarbonylamino,ethylcarbonylamino, propylcarbonylamino, 1-methylethylcarbonylamino,butylcarbonylamino, 1-methylpropylcarbonylamino,2-methylpropylcarbonylamino, 1,1-dimethylethylcarbonylamino,pentylcarbonylamino, 1-methylbutylcarbonylamino,2-methylbutylcarbonylamino, 3-methylbutylcarbonylamino,2,2-dimethylpropylcarbonylamino, 1-ethylpropylcarbonylamino,hexylcarbonylamino, 1,1-dimethylpropylcarbonylamino,1,2-dimethylpropylcarbonylamino, 1-methylpentylcarbonylamino,2-methylpentylcarbonylamino,3-methylpentylcarbonylamino,4-methylpentylcarbonylamino, 1,1-dimethylbutylcarbonylamino,1,2-dimethylbutylcarbonylamino, 1,3-dimethylbutylcarbonylamino,2,2-dimethylbutylcarbonylamino, 2,3-dimethylbutylcarbonylamino,3,3-dimethylbutylcarbonylamino, 1-ethylbutylcarbonylamino,2-ethylbutylcarbonylamino, 1,1,2-trimethylpropylcarbonylamino,1,2,2-trimethylpropylcarbonylamino, 1-ethyl(1-methylpropylcarbonylaminoand 1-ethyl-2-methylpropylcarbonylamino, preferably methylcarbonylaminoand ethylcarbonylamino, in particular ethylcarbonylamino;

C₃ -C₇ -cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl and cycloheptyl, preferably cyclopropyl, cyclopentyl andcyclohexyl, in particular cyclopropyl;

C₃ -C₇ -cycloalkoxy such as cyclopropoxy, cyclobutoxy, cyclopentoxy,cyclohexoxy and cycloheptoxy, preferably cyclopentoxy and cyclohexoxy,in particular cyclohexoxy;

C₃ -C₇ -cycloalkylthio such as cyclopropylthio, cyclobutylthio,cyclopentylthio, cyclohexylthio and cycloheptylthio, preferablycyclohexylthio;

C₃ -C₇ -cycloalkylamino such as cyclopropylamino, cyclobutylamino,cyclopentylamino, cyclohexylamino and cycloheptylamino, preferablycyclopropylamino and cyclohexylamino, in particular cyclopropylamino.

In addition to the abovementioned substituents, the mono- or binucleararomatic or heteroaromatic systems can also carry a radical -CR'=NOR",where the radicals R' and R" are the following groups:

R' is hydrogen, cyano, alkyl (preferably C₁ -C₆ -alkyl, in particular C₁-C₄ -alkyl), haloalkyl (preferably C₁ -C₄ -haloalkyl, in particular C₁-C₂ -haloalkyl), alkenyl (preferably C₂ -C₆ -alkenyl, in particular C₂-C₄ -alkenyl), haloalkenyl (preferably C₂ -C₆ -haloalkenyl, inparticular C₂ -C₄ -haloalkenyl), alkynyl (preferably C₂ -C₆ -alkynyl, inparticular C₂ -C₄ -alkynyl), haloalkynyl (preferably C₂ -C₆-haloalkynyl, in particular C₂ -C4-haloalkynyl) and cycloalkyl(preferably C₃ -C₈ -cycloalkyl, in particular C₃ -C₆ -cycloalkyl);

R" is alkyl (preferably C₁ -C₆ -alkyl, in particular C₁ -C₄ -alkyl),haloalkyl (preferably C₁ -C₄ -haloalkyl, in particular C₁ -C₂-haloalkyl), alkenyl (preferably C₂ -C₆ -alkenyl, in particular C₂ -C₄-alkenyl), haloalkenyl (preferably C₂ -C₆ -haloalkenyl, in particular C₂-C₄ -haloalkenyl), alkynyl (preferably C₂ -C₆ -alkynyl, in particular C₂-C₄ -alkynyl), haloalkynyl (preferably C₂ -C₆ -haloalkynyl, inparticular C₂ -C₄ -haloalkynyl) and cycloalkyl (preferably C₃ -C₈-cycloalkyl, in particular C3-C₆ -cycloalkyl).

With respect to their biological action, compounds I are preferred whereR is C₁ -C₄ -alkyl.

In addition, compounds I are preferred where R is halogen, in particularfluorine, chlorine and bromine.

Equally, compounds I are preferred where R is C₁ -C₄ -alkoxy.

Additionally, compounds I are preferred where R is cyano or nitro.

Equally, compounds I are preferred where R is C₁ -C₄ -haloalkyl (inparticular trifluoromethyl) or C₁ -C₄ -haloalkoxy (in particulartrifluoromethoxy).

Additionally, compounds I are preferred where R is a groupC(R^(a))═NOR^(b), where R^(a) and R^(b) in particular represent C₁ -C₄-alkyl groups.

In addition, compounds I are preferred where m is 1, 2 or 3, inparticular 1 or 2.

In addition, compounds I are preferred where R¹ is C₁ -C₄ -alkyl or C₁-C₄ -haloalkyl.

In addition, compounds I are preferred where R¹ is halogen (inparticular fluorine, chlorine or bromine).

Equally, compounds I are preferred where R¹ is cyano or nitro.

Additionally, compounds I are preferred where R¹ is C₁ -C₄ -alkoxy or C₁-C₄ -haloalkoxy.

In addition, compounds I are preferred where n is 0, 1 or 2 (inparticular 0 or 1).

In addition, compounds I are preferred where R² is C₁ -C₄ -alkyl or C₁-C₄ -haloalkyl.

In addition, compounds I are preferred where R² is halogen (inparticular fluorine, chlorine or bromine).

Equally, compounds I are preferred where R² is cyano or nitro.

Additionally, compounds I are preferred where R² is C₁ -C₄ -alkoxy or C₁-C₄ -haloalkoxy.

In addition compounds I are preferred where R³ is cyano, halogen, C₁ -C₄-alkyl, C₁ -C₂ -haloalkyl, C₁ -C₄ -alkoxy or C₁ -C₂ -haloalkoxy.

Equally, compounds I are preferred where o is 0 or 1,in particular 0.

In the case where o is not 0, compounds I are preferred where there is aradical R³ in the 3- or 6-position.

In addition, compounds I are preferred where R⁴ is hydrogen, C₁ -C₄-alkyl or C₁ -C₂ -haloalkyl.

Additionally, compounds I are preferred where R⁵ X is methyl, ethyl,methoxy or methylamino.

In particular, with respect to their use, the compounds I compiled inthe following tables are preferred. The groups mentioned for asubstituent in the tables are additionally considered per se(independently of the combination in which they are mentioned) to be aparticularly preferred embodiment of the substituents concerned.

Table 1

Compounds of the general formula I (o=0), where R⁴ is methyl, R⁵ X ishydrogen and the combination of the substituents R_(m), R¹ _(n) and R²for a compound in each case corresponds to one line of Table A.

Table 2

Compounds of the general formula I (o=0), where R⁴ is methyl, R⁵ X ismethyl and the combination of the substituents R_(m), R¹ _(n) and R² fora compound in each case corresponds to one line of Table A.

Table 3

Compounds of the general formula I (o=0), where R⁴ is methyl, R⁵ X isethyl and the combination of the substituents R_(m), R¹ _(n) and R² fora compound in each case corresponds to one line of Table A.

Table 4

Compounds of the general formula I (o=0), where R⁴ is methyl, R⁵ X ismethoxy and the combination of the substituents R_(m), R¹ _(n) and R²for a compound in each case corresponds to one line of Table A.

Table 5

Compounds of the general formula I (o=0), where R⁴ is methyl, R⁵ X ismethylamino and the combination of the substituents R_(m), R¹ _(n) andR² for a compound in each case corresponds to one line of Table A.

Table 6

Compounds of the general formula I (o=0), where R⁴ is ethyl, R⁵ X ishydrogen and the combination of the substituents R_(m), R¹ _(n) and R²for a compound in each case corresponds to one line of Table A.

Table 7

Compounds of the general formula I (o=0), where R⁴ is ethyl, R⁵ X ismethyl and the combination of the substituents R_(m), R¹ and R² for acompound in each case corresponds to one line of Table A.

Table 8

Compounds of the general formula I (o=0), where R⁴ is ethyl, R⁵ X isethyl and the combination of the substituents R_(m), R¹ _(n) and R² fora compound in each case corresponds to one line of Table A.

Table 9

Compounds of the general formula I (o=0), where R⁴ is ethyl, R⁵ X ismethoxy and the combination of the substituents R_(m), R¹ _(n) and R²for a compound in each case corresponds to one line of Table A.

Table 10

Compounds of the general formula I (o=0), where R⁴ is ethyl, R⁵ X ismethylamino and the combination of the substituents R_(m), R¹ _(n) andR² for a compound in each case corresponds to one line of Table A.

Table 11

Compounds of the general formula I (o=1), where R³ is 3-fluorine, R⁴ ismethyl, R⁵ X is hydrogen and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 12

Compounds of the general formula I (o=1), where R³ is 3-fluorine, R⁴ ismethyl, R⁵ X is methyl and the combination of the substituents R_(m), R¹_(n) and R² for a compound in each case corresponds to one line of TableA.

Table 13

Compounds of the general formula I (o=1), where R³ is 3-fluorine, R⁴ ismethyl, R⁵ X is ethyl and the combination of the substituents R_(m), R¹_(n) and R² for a compound in each case corresponds to one line of TableA.

Table 14

Compounds of the general formula I (o=1), where R³ is 3-fluorine, R⁴ ismethyl, R⁵ X is methoxy and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 15

Compounds of the general formula I (o=1), where R³ is 3-fluorine, R⁴ ismethyl, R⁵ X is methylamino and the combination of the substituentsR_(m), R¹ _(n) and R² for a compound in each case corresponds to oneline of Table A.

Table 16

Compounds of the general formula I (o=1), where R³ is 3-chlorine, R⁴ ismethyl, R⁵ X is hydrogen and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 17

Compounds of the general formula I (o=1), where R³ is 3-chlorine, R⁴ ismethyl, R⁵ X is methyl and the combination of the substituents R_(m), R¹I and R² for a compound in each case corresponds to one line of Table A.

Table 18

Compounds of the general formula I (o=1), where R³ is 3-chlorine, R⁴ ismethyl, R⁵ X is ethyl and the combination of the substituents R_(m), R¹_(n) and R² for a compound in each case corresponds to one line of TableA.

Table 19

Compounds of the general formula I (o=1), where R³ is 3chlorine, R⁴ ismethyl, R⁵ X is methoxy and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 20

Compounds of the general formula I (o=1), where R³ is 3-chlorine, R⁴ ismethyl, R⁵ X is methylamino and the combination of the substituentsR_(m), R¹ _(n) and R² for a compound in each case corresponds to oneline of Table A.

Table 21

Compounds of the general formula I (o=1), where R³ is 6-chlorine, R⁴ ismethyl, R⁵ X is hydrogen and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 22

Compounds of the general formula I (o=1), where R³ is 6-chlorine, R⁴ ismethyl, R⁵ X is methyl and the combination of the substituents R_(m), R¹_(n) and R² for a compound in each case corresponds to one line of TableA.

Table 23

Compounds of the general formula I (o=1), where R³ is 6-chlorine, R⁴ ismethyl, R⁵ X is ethyl and the combination of the substituents R_(m), R¹_(n) and R² for a compound in each case corresponds to one line of TableA.

Table 24

Compounds of the general formula I (o=1), where R³ is 6-chlorine, R⁴ ismethyl, R⁵ X is methoxy and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 25

Compounds of the general formula I (o=1), where R³ is 6-chlorine, R⁴ ismethyl, R⁵ X is methylamino and the combination of the substituentsR_(m), R¹ _(n) and R² for a compound in each case corresponds to oneline of Table A.

Table 26

Compounds of the general formula I (o=0), where R⁴ is hydrogen, R⁵ X ishydrogen and the combination of the substituents R_(m), R¹ _(n) and R²for a compound in each case corresponds to one line of Table A.

Table 27

Compounds of the general formula I (o=0), where R⁴ is hydrogen, R⁵ X ismethyl and the combination of the substituents R_(m), R¹ _(n) and R² fora compound in each case corresponds to one line of Table A.

Table 28

Compounds of the general formula I (o=0), where R⁴ is hydrogen, R⁵ X isethyl and the combination of the substituents R_(m), R¹ _(n) and R² fora compound in each case corresponds to one line of Table A.

Table 29

Compounds of the general formula I (o=0), where R⁴ is hydrogen, R⁵ X ismethoxy and the combination of the substituents R_(m), R¹ _(n) and R²for a compound in each case corresponds to one line of Table A.

Table 30

Compounds of the general formula I (o=0), where R⁴ is hydrogen, R⁵ X ismethylamino and the combination of the substituents R_(m), R¹ _(n) andR² for a compound in each case corresponds to one line of Table A.

Table 31

Compounds of the general formula I (o=1), where R³ is 6-methyl, R⁴ ismethyl, R⁵ X is hydrogen and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 32

Compounds of the general formula I (o=1), where R³ is 6-methyl, R⁴ ismethyl, R⁵ X is methyl and the combination of the substituents R_(m), R¹_(n) and R² for a compound in each case corresponds to one line of TableA.

Table 33

Compounds of the general formula I (o=1), where R³ is 6-methyl, R⁴ ismethyl, R⁵ X is ethyl and the combination of the substituents R_(m), R¹_(n) and R² for a compound in each case corresponds to one line of TableA.

Table 34

Compounds of the general formula I (o=1), where R³ is 6-methyl, R⁴ ismethyl, R⁵ X is methoxy and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 35

Compounds of the general formula I (o=1), where R³ is 6-methyl, R⁴ ismethyl, R⁵ X is methylamino and the combination of the substituentsR_(m), R¹ _(n) and R² for a compound in each case corresponds to oneline of Table A.

Table 36

Compounds of the general formula I (o=1), where R³ is 6-methyl, R⁴ ishydrogen, R⁵ X is hydrogen and the combination of the substituentsR_(m), R¹ _(n) and R² for a compound in each case corresponds to oneline of Table A.

Table 37

Compounds of the general formula I (o=1), where R³ is 6-methyl, R⁴ ishydrogen, R⁵ X is methyl and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 38

Compounds of the general formula I (o=1), where R³ is 6-methyl, R⁴ ishydrogen, R⁵ X is ethyl and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 39

Compounds of the general formula I (o=1), where R³ is 6-methyl, R⁴ ishydrogen, R⁵ X is methoxy and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 40

Compounds of the general formula I (o=1), where R³ is 6-methyl, R⁴ ishydrogen, R⁵ X is methylamino and the combination of the substituentsR_(m), R¹ _(n) and R² for a compound in each case corresponds to oneline of Table A.

Table 41

Compounds of the general formula I (o=1), where R³ is 6-chlorine, R⁴ ishydrogen, R⁵ X is hydrogen and the combination of the substituentsR_(m), R¹, and R² for a compound in each case corresponds to one line ofTable A.

Table 42

Compounds of the general formula I (o=1), where R³ is 6-chlorine, R⁴ ishydrogen, R⁵ X is methyl and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 43

Compounds of the general formula I (o=1), where R³ is 6-chlorine, R⁴ ishydrogen, R⁵ X is ethyl and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 44

Compounds of the general formula I (o=1), where R³ is 6-chlorine, R⁴ ishydrogen, R⁵ X is methoxy and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 45

Compounds of the general formula I (o=1), where R³ is 6-chlorine, R⁴ ishydrogen, R⁵ X is methylamino and the combination of the substituentsR_(m), R¹ and R² for a compound in each case corresponds to one line ofTable A.

Table 46

Compounds of the general formula I (o=1), where R³ is 3-chlorine, R⁴ ishydrogen, R⁵ X is hydrogen and the combination of the substituentsR_(m), R¹ _(n) and R² for a compound in each case corresponds to oneline of Table A.

Table 47

Compounds of the general formula I (o=1), where R³ is 3-chlorine, R⁴ ishydrogen, R⁵ X is methyl and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 48

Compounds of the general formula I (o=1), where R³ is 3-chlorine, R⁴ ishydrogen, R⁵ X is ethyl and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 49

Compounds of the general formula I (o=1), where R³ is 3-chlorine, R⁴ ishydrogen, R⁵ X is methoxy and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 50

Compounds of the general formula I (o=1), where R³ is 3-chlorine, R⁴ ishydrogen, R⁵ X is methylamino and the combination of the substituentsR_(m), R¹ _(n) and R² for a compound in each case corresponds to oneline of Table A.

Table 51

Compounds of the general formula I (o=1), where R³ is 3-fluorine, R⁴ ishydrogen, R⁵ X is hydrogen and the combination of the substituentsR_(m), R¹ _(n) and R² for a compound in each case corresponds to oneline of Table A.

Table 52

Compounds of the general formula I (o=1), where R³ is 3-fluorine, R⁴ ishydrogen, R⁵ X is methyl and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 53

Compounds of the general formula I (o=1), where R³ is 3-fluorine, R⁴ ishydrogen, R⁵ X is ethyl and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 54

Compounds of the general formula I (o=1), where R³ is 3-fluorine, R⁴ ishydrogen, R⁵ X is methoxy and the combination of the substituents R_(m),R¹ _(n) and R² for a compound in each case corresponds to one line ofTable A.

Table 55

Compounds of the general formula I (o=1), where R³ is 3-fluorine, R⁴ ishydrogen, R⁵ X is methylamino and the combination of the substituentsR_(m), R¹ _(n) and R² for a compound in each case corresponds to oneline of Table A.

                  TABLE A                                                         ______________________________________                                        Number R.sub.m             R.sup.2  R.sup.1.sub.n                             ______________________________________                                         12    2-F                 CH.sub.3 H                                          13    3-F                 CH.sub.3 H                                          14    4-F                 CH.sub.3 H                                          15    2,4-F.sub.2         CH.sub.3 H                                          16    2,4,6-F.sub.3       CH.sub.3 H                                          17    2,3,4,5,6-F.sub.5   CH.sub.3 H                                          18    2,3-F.sub.2         CH.sub.3 H                                          19    2-Cl                CH.sub.3 H                                          20    3-Cl                CH.sub.3 H                                          21    4-Cl                CH.sub.3 H                                          22    2,3-Cl.sub.2        CH.sub.3 H                                          23    2,4-Cl.sub.2        CH.sub.3 H                                          24    2,5-Cl.sub.2        CH.sub.3 H                                          25    2,6-Cl.sub.2        CH.sub.3 H                                          26    3,4-Cl.sub.2        CH.sub.3 H                                          27    3,5-Cl.sub.2        CH.sub.3 H                                          28    2,3,4-Cl.sub.3      CH.sub.3 H                                          29    2,3,5-Cl.sub.3      CH.sub.3 H                                          30    2,3,6-Cl.sub.3      CH.sub.3 H                                          31    2,4,5-Cl.sub.3      CH.sub.3 H                                          32    2,4,6-Cl.sub.3      CH.sub.3 H                                          33    3,4,5-Cl.sub.3      CH.sub.3 H                                          34    2,3,4,6-Cl.sub.4    CH.sub.3 H                                          35    2,3,5,6-Cl.sub.4    CH.sub.3 H                                          36    2,3,4,5,6-Cl.sub.5  CH.sub.3 H                                          37    2-Br                CH.sub.3 H                                          38    3-Br                CH.sub.3 H                                          39    4-Br                CH.sub.3 H                                          40    2,4-Br.sub.2        CH.sub.3 H                                          41    2,5-Br.sub.2        CH.sub.3 H                                          42    2,6-Br.sub.2        CH.sub.3 H                                          43    2,4,6-Br.sub.3      CH.sub.3 H                                          44    2,3,4,5,6-Br.sub.5  CH.sub.3 H                                          45    2-I                 CH.sub.3 H                                          46    3-I                 CH.sub.3 H                                          47    4-I                 CH.sub.3 H                                          48    2,4-I.sub.2         CH.sub.3 H                                          49    2-Cl, 3-F           CH.sub.3 H                                          50    2-Cl, 4-F           CH.sub.3 H                                          51    2-Cl, 5-F           CH.sub.3 H                                          52    2-Cl, 6-F           CH.sub.3 H                                          53    2-Cl, 3-Br          CH.sub.3 H                                          54    2-Cl, 4-Br          CH.sub.3 H                                          55    2-Cl, 5-Br          CH.sub.3 H                                          56    2-Cl, 6-Br          CH.sub.3 H                                          57    2-Br, 3-Cl          CH.sub.3 H                                          58    2-Br, 4-Cl          CH.sub.3 H                                          59    2-Br, 5-Cl          CH.sub.3 H                                          60    2-Br, 3-F           CH.sub.3 H                                          61    2-Br, 4-F           CH.sub.3 H                                          62    2-Br, 5-F           CH.sub.3 H                                          63    2-Br, 6-F           CH.sub.3 H                                          64    2-F, 3-Cl           CH.sub.3 H                                          65    2-F, 4-Cl           CH.sub.3 H                                          66    2-F, 5-Cl           CH.sub.3 H                                          67    3-Cl, 4-F           CH.sub.3 H                                          68    3-Cl, 5-F           CH.sub.3 H                                          69    3-Cl, 4-Br          CH.sub.3 H                                          70    3-Cl, 5-Br          CH.sub.3 H                                          71    3-F, 4-Cl           CH.sub.3 H                                          72    3-F, 4-Br           CH.sub.3 H                                          73    3-Br, 4-Cl          CH.sub.3 H                                          74    3-Br, 4-F           CH.sub.3 H                                          75    2,6-Cl.sub.2, 4-Br  CH.sub.3 H                                          76    2-CH.sub.3          CH.sub.3 H                                          77    3-CH.sub.3          CH.sub.3 H                                          78    4-CH.sub.3          CH.sub.3 H                                          79    2,3-(CH.sub.3).sub.2                                                                              CH.sub.3 H                                          80    2,4-(CH.sub.3).sub.2                                                                              CH.sub.3 H                                          81    2,5-(CH.sub.3).sub.2                                                                              CH.sub.3 H                                          82    2,6-(CH.sub.3).sub.2                                                                              CH.sub.3 H                                          83    3,4-(CH.sub.3).sub.2                                                                              CH.sub.3 H                                          84    3,5-(CH.sub.3).sub.2                                                                              CH.sub.3 H                                          85    2,3,5-(CH.sub.3).sub.3                                                                            CH.sub.3 H                                          86    2,3,4-(CH.sub.3).sub.3                                                                            CH.sub.3 H                                          87    2,3,6-(CH.sub.3).sub.3                                                                            CH.sub.3 H                                          88    2,4,5-(CH.sub.3).sub.3                                                                            CH.sub.3 H                                          89    2,4,6-(CH.sub.3).sub.3                                                                            CH.sub.3 H                                          90    3,4,5-(CH.sub.3).sub.3                                                                            CH.sub.3 H                                          91    2,3,4,6-(CH.sub.3).sub.4                                                                          CH.sub.3 H                                          92    2,3,5,6-(CH.sub.3).sub.4                                                                          CH.sub.3 H                                          93    2,3,4,5,6-(CH.sub.3).sub.5                                                                        CH.sub.3 H                                          94    2-C.sub.2 H.sub.5   CH.sub.3 H                                          95    3-C.sub.2 H.sub.5   CH.sub.3 H                                          96    4-C.sub.2 H.sub.5   CH.sub.3 H                                          97    2,4-(C.sub.2 H.sub.5).sub.5                                                                       CH.sub.3 H                                          98    2,6-(C.sub.2 H.sub.5).sub.2                                                                       CH.sub.3 H                                          99    3,5-(C.sub.2 H.sub.5).sub.2                                                                       CH.sub.3 H                                         100    2,4,6-(C.sub.2 H.sub.5).sub.3                                                                     CH.sub.3 H                                         101    2-n-C.sub.3 H.sub.7 CH.sub.3 H                                         102    3-n-C.sub.3 H.sub.7 CH.sub.3 H                                         103    4-n-C.sub.3 H.sub.7 CH.sub.3 H                                         104    2-i-C.sub.3 H.sub.7 CH.sub.3 H                                         105    3-i-C.sub.3 H.sub.7 CH.sub.3 H                                         106    4-i-C.sub.3 H.sub.7 CH.sub.3 H                                         107    2,4-(i-C.sub.3 H.sub.7).sub.2                                                                     CH.sub.3 H                                         108    2,6-(i-C.sub.3 H.sub.7).sub.2                                                                     CH.sub.3 H                                         109    3,5-(i-C.sub.3 H.sub.7).sub.2                                                                     CH.sub.3 H                                         110    2-s-C.sub.4 H.sub.9 CH.sub.3 H                                         111    3-s-C.sub.4 H.sub.9 CH.sub.3 H                                         112    4-s-C.sub.4 H.sub.9 CH.sub.3 H                                         113    2-t-C.sub.4 H.sub.9 CH.sub.3 H                                         114    3-t-C.sub.4 H.sub.9 CH.sub.3 H                                         115    4-t-C.sub.4 H.sub.9 CH.sub.3 H                                         116    4-n-C.sub.9 H.sub.19                                                                              CH.sub.3 H                                         117    2-CH.sub.3, 4-t-C.sub.4 H.sub.9                                                                   CH.sub.3 H                                         118    2-CH.sub.3, 6-t-C.sub.4 H.sub.9                                                                   CH.sub.3 H                                         119    2-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                   CH.sub.3 H                                         120    2-CH.sub.3, 5-i-C.sub.3 H.sub.7                                                                   CH.sub.3 H                                         121    3-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                   CH.sub.3 H                                         122    2-cyclo-C.sub.6 H.sub.11                                                                          CH.sub.3 H                                         123    3-cyclo-C.sub.6 H.sub.11                                                                          CH.sub.3 H                                         124    4-cyclo-C.sub.6 H.sub.11                                                                          CH.sub.3 H                                         125    2-Cl, 4-C.sub.6 H.sub.5                                                                           CH.sub.3 H                                         126    2-Br, 4-C.sub.6 H.sub.5                                                                           CH.sub.3 H                                         127    2-OCH.sub.3         CH.sub.3 H                                         128    3-OCH.sub.3         CH.sub.3 H                                         129    4-OCH.sub.3         CH.sub.3 H                                         130    2-OC.sub.2 H.sub.5  CH.sub.3 H                                         131    3-O--C.sub.2 H.sub.5                                                                              CH.sub.3 H                                         132    4-O--C.sub.2 H.sub.5                                                                              CH.sub.3 H                                         133    2-O-n-C.sub.3 H.sub.7                                                                             CH.sub.3 H                                         134    3-O-n-C.sub.3 H.sub.7                                                                             CH.sub.3 H                                         135    4-O-n-C.sub.3 H.sub.7                                                                             CH.sub.3 H                                         136    2-O-i-C.sub.3 H.sub.7                                                                             CH.sub.3 H                                         137    3-O-i-C.sub.3 H.sub.7                                                                             CH.sub.3 H                                         138    4-O-i-C.sub.3 H.sub.7                                                                             CH.sub.3 H                                         139    2-O-n-C.sub.6 H.sub.13                                                                            CH.sub.3 H                                         140    3-O-n-C.sub.6 H.sub.13                                                                            CH.sub.3 H                                         141    4-O-n-C.sub.6 H.sub.13                                                                            CH.sub.3 H                                         142    2-O--CH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.3 H                                         143    3-O--CH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.3 H                                         144    4-O--CH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.3 H                                         145    2-O--(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                             CH.sub.3 H                                         146    4-O--(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                             CH.sub.3 H                                         147    2,3-(OCH.sub.3).sub.2                                                                             CH.sub.3 H                                         148    2,4-(OCH.sub.3).sub.2                                                                             CH.sub.3 H                                         149    2,5-(OCH.sub.3).sub.2                                                                             CH.sub.3 H                                         150    2,6-(OCH.sub.3).sub.2                                                                             CH.sub.3 H                                         151    3,4-(OCH.sub.3).sub.2                                                                             CH.sub.3 H                                         152    3,5-(OCH.sub.3).sub.2                                                                             CH.sub.3 H                                         153    2-O-t-C.sub.4 H.sub.9                                                                             CH.sub.3 H                                         154    3-O-t-C.sub.4 H.sub.9                                                                             CH.sub.3 H                                         155    4-O-t-C.sub.4 H.sub.9                                                                             CH.sub.3 H                                         156    3-(3'-Cl--C.sub.6 H.sub.4)                                                                        CH.sub.3 H                                         157    4-(4'-CH.sub.3 --C.sub.6 H.sub.4)                                                                 CH.sub.3 H                                         158    2-O--C.sub.6 H.sub.5                                                                              CH.sub.3 H                                         159    3-O--C.sub.6 H.sub.5                                                                              CH.sub.3 H                                         160    4-O--C.sub.6 H.sub.5                                                                              CH.sub.3 H                                         161    2-O-(2'-F--C.sub.6 H.sub.4)                                                                       CH.sub.3 H                                         162    3-O-(3'-Cl--C.sub.6 H.sub.4)                                                                      CH.sub.3 H                                         163    4-O-(4'-CH.sub.3 --C.sub.6 H.sub.4)                                                               CH.sub.3 H                                         164    2,3,6-(CH.sub.3).sub.3, 4-F                                                                       CH.sub.3 H                                         165    2,3,6-(CH.sub.3).sub.3, 4-Cl                                                                      CH.sub.3 H                                         166    2,3,6-(CH.sub.3).sub.3, 4-Br                                                                      CH.sub.3 H                                         167    2,4-(CH.sub.3).sub.2, 6-F                                                                         CH.sub.3 H                                         168    2,4-(CH.sub.3).sub.2, 6-Cl                                                                        CH.sub.3 H                                         169    2,4-(CH.sub.3).sub.2, 6-Br                                                                        CH.sub.3 H                                         170    2-i-CH.sub.3 H.sub.1, 4-Cl, 5-CH.sub.3                                                            CH.sub.3 H                                         171    2-Cl, 4-NO.sub.2    CH.sub.3 H                                         172    2-NO.sub.2, 4-Cl    CH.sub.3 H                                         173    2-OCH.sub.3, 5-NO.sub.2                                                                           CH.sub.3 H                                         174    2,4-Cl.sub.2, 5-NO.sub.2                                                                          CH.sub.3 H                                         175    2,4-Cl.sub.2, 6-NO.sub.2                                                                          CH.sub.3 H                                         176    2,6-Cl.sub.2, 4-NO.sub.2                                                                          CH.sub.3 H                                         177    2,6-Br.sub.2, 4-NO.sub.2                                                                          CH.sub.3 H                                         178    2,6-I.sub.2, 4-NO.sub.2                                                                           CH.sub.3 H                                         179    2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl                                                             CH.sub.3 H                                         180    2-CO.sub.2 CH.sub.3 CH.sub.3 H                                         181    3-CO.sub.2 CH.sub.3 CH.sub.3 H                                         182    4-CO.sub.2 CH.sub.3 CH.sub.3 H                                         183    2-CH.sub.2 --OCH.sub.3                                                                            CH.sub.3 H                                         184    3-CH.sub.2 --OCH.sub.3                                                                            CH.sub.3 H                                         185    4-CH.sub.2 --OCH.sub.3                                                                            CH.sub.3 H                                         186    2-Me-4-CH.sub.3 --CH(CH.sub.3)--CO                                                                CH.sub.3 H                                         187    2-CH.sub.3 -4-(CH.sub.3 --C═NOCH.sub.3)                                                       CH.sub.3 H                                         188    2-CH.sub.3 -4-(CH.sub.3 --C═NOC.sub.2 H.sub.5)                                                CH.sub.3 H                                         189    2-CH.sub.3 -4-(CH.sub.3 --C═NO-n-C.sub.3 H.sub.7)                                             CH.sub.3 H                                         190    2-CH.sub.3 -4-(CH.sub.3 --C═NO-i-C.sub.3 H.sub.7)                                             CH.sub.3 H                                         191    2,5-(CH.sub.3)2-4-(CH.sub.3 --C═NOCH.sub.3)                                                   CH.sub.3 H                                         192    2,5-(CH.sub.3)2-4-(CH.sub.3 --C═NOC.sub.2 H.sub.5)                                            CH.sub.3 H                                         193    2,5-(CH.sub.3 -4-(CH.sub.3 --C═NO-n-C.sub.3 H.sub.7)                                          CH.sub.3 H                                         194    2,5-(CH.sub.3).sub.2 -4-(CH.sub.3 --C═NO-i-C.sub.3 H.sub.7)                                   CH.sub.3 H                                         195    2-C.sub.6 H.sub.5   CH.sub.3 H                                         196    3-C.sub.6 H.sub.5   CH.sub.3 H                                         197    4-C.sub.6 H.sub.5   CH.sub.3 H                                         198    2-(2'-F--C.sub.6 H.sub.4)                                                                         CH.sub.3 H                                         199    2-CH.sub.3, 5-Br    CH.sub.3 H                                         200    2-CH.sub.3, 6-Br    CH.sub.3 H                                         201    2-Cl, 3-CH.sub.3    CH.sub.3 H                                         202    2-Cl, 4-CH.sub.3    CH.sub.3 H                                         203    2-Cl, 5-CH.sub.3    CH.sub.3 H                                         204    2-F, 3-CH.sub.3     CH.sub.3 H                                         205    2-F, 4-CH.sub.3     CH.sub.3 H                                         206    2-F, 5-CH.sub.3     CH.sub.3 H                                         207    2-Br, 3-CH.sub.3    CH.sub.3 H                                         208    2-Br, 4-CH.sub.3    CH.sub.3 H                                         209    2-Br, 5-CH.sub.3    CH.sub.3 H                                         210    3-CH.sub.3, 4-Cl    CH.sub.3 H                                         211    3-CH.sub.3, 5-Cl    CH.sub.3 H                                         212    3-CH.sub.3, 4-F     CH.sub.3 H                                         213    3-CH.sub.3, 5-F     CH.sub.3 H                                         214    3-CH.sub.3, 4-Br    CH.sub.3 H                                         215    3-CH.sub.3, 5-Br    CH.sub.3 H                                         216    3-F, 4-CH.sub.3     CH.sub.3 H                                         217    3-Cl, 4-CH.sub.3    CH.sub.3 H                                         218    3-Br, 4-CH.sub.3    CH.sub.3 H                                         219    2-Cl, 4,5-(CH.sub.3).sub.2                                                                        CH.sub.3 H                                         220    2-Br, 4,5-(CH.sub.3).sub.2                                                                        CH.sub.3 H                                         221    2-Cl, 3,5-(CH.sub.3).sub.2                                                                        CH.sub.3 H                                         222    2-Br, 3,5-(CH.sub.3).sub.2                                                                        CH.sub.3 H                                         223    2,6-Cl.sub.2, 4-CH.sub.3                                                                          CH.sub.3 H                                         224    2,6-F.sub.2, 4-CH.sub.3                                                                           CH.sub.3 H                                         225    2,6-Br.sub.2, 4-CH.sub.3                                                                          CH.sub.3 H                                         226    2,4-Br.sub.2, 6-CH.sub.3                                                                          CH.sub.3 H                                         227    2,4-F.sub.2, 6-CH.sub.3                                                                           CH.sub.3 H                                         226    2,4-Br.sub.2, 6-CH.sub.3                                                                          CH.sub.3 H                                         229    2,6-(CH.sub.3).sub.2, 4-F                                                                         CH.sub.3 H                                         230    2,6-(CH.sub.3).sub.2, 4-Cl                                                                        CH.sub.3 H                                         231    2,6-(CH.sub.3).sub.2, 4-Br                                                                        CH.sub.3 H                                         232    3,5-(CH.sub.3).sub.2, 4-F                                                                         CH.sub.3 H                                         233    3,5-(CH.sub.3).sub.2, 4-Cl                                                                        CH.sub.3 H                                         234    3,5-(CH.sub.3).sub.2, 4-Br                                                                        CH.sub.3 H                                         235    2-CF.sub.3          CH.sub.3 H                                         236    3-CF.sub.3          CH.sub.3 H                                         237    4-CF.sub.3          CH.sub.3 H                                         238    2-OCF.sub.3         CH.sub.3 H                                         239    3-OCF.sub.3         CH.sub.3 H                                         240    4-OCF.sub.3         CH.sub.3 H                                         241    3-OCH.sub.2 CHF.sub.2                                                                             CH.sub.3 H                                         242    2-NO.sub.2          CH.sub.3 H                                         243    3-NO.sub.2          CH.sub.3 H                                         244    4-NO.sub.2          CH.sub.3 H                                         245    2-CN                CH.sub.3 H                                         246    3-CN                CH.sub.3 H                                         247    4-CN                CH.sub.3 H                                         248    2-CH.sub.3, 3-Cl    CH.sub.3 H                                         249    2-CH.sub.3, 4-Cl    CH.sub.3 H                                         250    2-CH.sub.3, 5-Cl    CH.sub.3 H                                         251    2-CH.sub.3, 6-Cl    CH.sub.3 H                                         252    2-CH.sub.3, 3-F     CH.sub.3 H                                         253    2-CH.sub.3, 4-F     CH.sub.3 H                                         254    2-CH.sub.3, 5-F     CH.sub.3 H                                         255    2-CH.sub.3, 6-F     CH.sub.3 H                                         256    2-CH.sub.3, 3-Br    CH.sub.3 H                                         257    2-CH.sub.3, 4-Br    CH.sub.3 H                                         258    2-Pyridyl-2'        CH.sub.3 H                                         259    3-Pyridyl-3'        CH.sub.3 H                                         260    4-Pyridyl-4'        CH.sub.3 H                                         261    2-CO--CH.sub.3      CH.sub.3 H                                         262    3-CO--CH.sub.3      CH.sub.3 H                                         263    4-CO--CH.sub.3      CH.sub.3 H                                         264    2-C(═N--OCH.sub.3)--CH.sub.3                                                                  CH.sub.3 H                                         265    3-C(═N--OCH.sub.3)--CH.sub.3                                                                  CH.sub.3 H                                         266    4-C(═N--OCH.sub.3)--CH.sub.3                                                                  CH.sub.3 H                                         267    2-F                 F        H                                         268    3-F                 F        H                                         269    4-F                 F        H                                         270    2,4-F.sub.2         F        H                                         271    2,4,6-F.sub.3       F        H                                         272    2,3,4,5,6-F.sub.5   F        H                                         273    2,3-F.sub.2         F        H                                         274    2-Cl                F        H                                         275    3-Cl                F        H                                         276    4-Cl                F        H                                         277    2,3-Cl.sub.2        F        H                                         278    2,4-Cl.sub.2        F        H                                         279    2,5-Cl.sub.2        F        H                                         280    2,6-Cl.sub.2        F        H                                         281    3,4-Cl.sub.2        F        H                                         282    3,5-Cl.sub.2        F        H                                         283    2,3,4-Cl.sub.3      F        H                                         284    2,3,5-Cl.sub.3      F        H                                         285    2,3,6-Cl.sub.3      F        H                                         286    2,4,5-Cl.sub.3      F        H                                         287    2,4,6-Cl.sub.3      F        H                                         288    3,4,5-Cl.sub.3      F        H                                         289    2,3,4,6-Cl.sub.4    F        H                                         290    2,3,5,6-Cl.sub.4    F        H                                         291    2,3,4,5,6-Cl.sub.5  F        H                                         292    2-Br                F        H                                         293    3-Br                F        H                                         294    4-Br                F        H                                         295    2,4-Br.sub.2        F        H                                         296    2,5-Br.sub.2        F        H                                         297    2,6-Br.sub.2        F        H                                         298    2,4,6-Br.sub.3      F        H                                         299    2,3,4,5,6-Br.sub.5  F        H                                         300    2-I                 F        H                                         301    3-I                 F        H                                         302    4-I                 F        H                                         303    2,4-I.sub.2         F        H                                         304    2-Cl, 3-F           F        H                                         305    2-Cl, 4-F           F        H                                         306    2-Cl, 5-F           F        H                                         307    2-Cl, 6-F           F        H                                         308    2-Cl, 3-Br          F        H                                         309    2-Cl, 4-Br          F        H                                         310    2-Cl, 5-Br          F        H                                         311    2-Cl, 6-Br          F        H                                         312    2-Br, 3-Cl          F        H                                         313    2-Br, 4-Cl          F        H                                         314    2-Br, 5-Cl          F        H                                         315    2-Br, 3-F           F        H                                         316    2-Br, 4-F           F        H                                         317    2-Br, 5-F           F        H                                         318    2-Br, 6-F           F        H                                         319    2-F, 3-Cl           F        H                                         320    2-F, 4-Cl           F        H                                         321    2-F, 5-Cl           F        H                                         322    3-Cl, 4-F           F        H                                         323    3-Cl, 5-F           F        H                                         324    3-Cl, 4-Br          F        H                                         325    3-Cl, 5-Br          F        H                                         326    3-F, 4-Cl           F        H                                         327    3-F, 4-Br           F        H                                         328    3-Br, 4-Cl          F        H                                         329    3-Br, 4-F           F        H                                         330    2,6-Cl.sub.2, 4-Br  F        H                                         331    2-CH.sub.3          F        H                                         332    3-CH.sub.3          F        H                                         333    4-CH.sub.3          F        H                                         334    2,3-(CH.sub.3).sub.2                                                                              F        H                                         335    2,4-(CH.sub.3).sub.2                                                                              F        H                                         336    2,5-(CH.sub.3).sub.2                                                                              F        H                                         337    2,6-(CH.sub.3).sub.2                                                                              F        H                                         338    3,4-(CH.sub.3).sub.2                                                                              F        H                                         339    3,5-(CH.sub.3).sub.2                                                                              F        H                                         340    2,3,5-(CH.sub.3).sub.3                                                                            F        H                                         341    2,3,4-(CH.sub.3).sub.3                                                                            F        H                                         342    2,3,6-(CH.sub.3).sub.3                                                                            F        H                                         343    2,4,5-(CH.sub.3).sub.3                                                                            F        H                                         344    2,416-(CH.sub.3).sub.3                                                                            F        H                                         345    3,4,5-(CH.sub.3).sub.3                                                                            F        H                                         346    2,3,4,6-(CH.sub.3).sub.4                                                                          F        H                                         347    2,3,5,6-(CH.sub.3).sub.4                                                                          F        H                                         348    2,3,4,5,6-(CH.sub.3).sub.5                                                                        F        H                                         349    2-C.sub.2 H.sub.5   F        H                                         350    3-C.sub.2 H.sub.5   F        H                                         351    4-C.sub.2 H.sub.5   F        H                                         352    2,4-(C.sub.2 H.sub.5).sub.5                                                                       F        H                                         353    2,6-(C.sub.2 H.sub.5).sub.2                                                                       F        H                                         354    3,5-(C.sub.2 H.sub.5).sub.2                                                                       F        H                                         355    2,4,6-(C.sub.2 H.sub.5).sub.3                                                                     F        H                                         356    2-n-C.sub.3 H.sub.7 F        H                                         357    3-n-C.sub.3 H.sub.7 F        H                                         358    4-n-C.sub.3 H.sub.7 F        H                                         359    2-i-C.sub.3 H.sub.7 F        H                                         360    3-i-C.sub.3 H.sub.7 F        H                                         361    4-i-C.sub.3 H.sub.7 F        H                                         362    2,4-(i-C.sub.3 H.sub.7).sub.2                                                                     F        H                                         363    2,6-(i-C.sub.3 H.sub.7).sub.2                                                                     F        H                                         364    3,5-(i-C.sub.3 H.sub.7).sub.2                                                                     F        H                                         365    2-s-C.sub.4 H.sub.9 F        H                                         366    3-s-C.sub.4 H.sub.9 F        H                                         367    4-s-C.sub.4 H.sub.9 F        H                                         368    2-t-C.sub.4 H.sub.9 F        H                                         369    3-t-C.sub.4 H.sub.9 F        H                                         370    4-t-C.sub.4 H.sub.9 F        H                                         371    4-n-C.sub.9 H.sub.19                                                                              F        H                                         372    2-CH.sub.3, 4-t-C.sub.4 H.sub.9                                                                   F        H                                         373    2-CH.sub.3, 6-t-C.sub.4 H.sub.9                                                                   F        H                                         374    2-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                   F        H                                         375    2-CH.sub.3, 5-i-C.sub.3 H.sub.7                                                                   F        H                                         376    3-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                   F        H                                         377    2-cyclo-C.sub.6 H.sub.11                                                                          F        H                                         378    3-cyclo-C.sub.6 H.sub.11                                                                          F        H                                         379    4-cyclo-C.sub.6 H.sub.11                                                                          F        H                                         380    2-Cl, 4-C.sub.6 H.sub.5                                                                           F        H                                         381    2-Br, 4-C.sub.6 H.sub.5                                                                           F        H                                         382    2-OCH.sub.3         F        H                                         383    3-OCH.sub.3         F        H                                         384    4-OCH.sub.3         F        H                                         385    2-0C.sub.2 H.sub.5  F        H                                         386    3-O--C.sub.2 H.sub.5                                                                              F        H                                         387    4-O--C.sub.2 H.sub.5                                                                              F        H                                         388    2-O-n-C.sub.3 H.sub.7                                                                             F        H                                         389    3-O-n-C.sub.3 H.sub.7                                                                             F        H                                         390    4-O-n-C.sub.3 H.sub.7                                                                             F        H                                         391    2-O-i-C.sub.3 H.sub.7                                                                             F        H                                         392    3-O-i-C.sub.3 H.sub.7                                                                             F        H                                         393    4-O-i-C.sub.3 H.sub.7                                                                             F        H                                         394    2-O-n-C.sub.6 H.sub.13                                                                            F        H                                         395    3-O-n-C.sub.6 H.sub.13                                                                            F        H                                         396    4-O-n-C.sub.6 H.sub.13                                                                            F        H                                         397    2-O--CH.sub.2 C.sub.6 H.sub.5                                                                     F        H                                         398    3-O--CH.sub.2 C.sub.6 H.sub.5                                                                     F        H                                         399    4-O--CH.sub.2 C.sub.6 H.sub.5                                                                     F        H                                         400    2-O--(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                             F        H                                         401    4-O--(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                             F        H                                         402    2,3-(OCH.sub.3).sub.2                                                                             F        H                                         403    2,4-(OCH.sub.3).sub.2                                                                             F        H                                         404    2,5-(OCH.sub.3).sub.2                                                                             F        H                                         405    2,6-(OCH.sub.3).sub.2                                                                             F        H                                         406    3,4-(OCH.sub.3).sub.2                                                                             F        H                                         407    3,5-(OCH.sub.3).sub.2                                                                             F        H                                         408    2-O-t-C.sub.4 H.sub.9                                                                             F        H                                         409    3-O-t-C.sub.4 H.sub.9                                                                             F        H                                         410    4-O-t-C.sub.4 H.sub.9                                                                             F        H                                         411    3-(3'-Cl--C.sub.6 H.sub.4)                                                                        F        H                                         412    4-(4'-CH.sub.3 --C.sub.6 H.sub.4)                                                                 F        H                                         413    2-O--C.sub.6 H.sub.5                                                                              F        H                                         414    3-O--C.sub.6 H.sub.5                                                                              F        H                                         415    4-O--C.sub.6 H.sub.5                                                                              F        H                                         416    2-O-(2'-F--C.sub.6 H.sub.4)                                                                       F        H                                         417    3-O-(3'-Cl--C.sub.6 H.sub.4)                                                                      F        H                                         418    4-O-(4'-CH.sub.3 --C.sub.6 H.sub.4)                                                               F        H                                         419    2,3,6-(CH.sub.3).sub.3, 4-F                                                                       F        H                                         420    2,3,6-(CH.sub.3).sub.3, 4-Cl                                                                      F        H                                         421    2,3,6-(CH.sub.3).sub.3, 4-Br                                                                      F        H                                         422    2,4-(CH.sub.3)2, 6-F                                                                              F        H                                         423    2,4-(CH.sub.3)2, 6-Cl                                                                             F        H                                         424    2,4-(CH.sub.3)2, 6-Br                                                                             F        H                                         425    2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3                                                             F        H                                         426    2-Cl, 4-NO.sub.2    F        H                                         427    2-NO.sub.2, 4-Cl    F        H                                         428    2-OCH.sub.3, 5-NO.sub.2                                                                           F        H                                         429    2,4-Cl.sub.2, 5-NO.sub.2                                                                          F        H                                         430    2,4-Cl.sub.2, 6-NO.sub.2                                                                          F        H                                         431    2,6-Cl.sub.2, 4-NO.sub.2                                                                          F        H                                         432    2,6-Br.sub.2, 4-NO.sub.2                                                                          F        H                                         433    2,6-I.sub.2, 4-NO.sub.2                                                                           F        H                                         434    2-CH.sub.3, 5-i-C.sub.3 H.sub.7,, 4-Cl                                                            F        H                                         435    2-CO.sub.2 CH.sub.3 F        H                                         436    3-CO.sub.2 CH.sub.3 F        H                                         437    4-CO.sub.2 CH.sub.3 F        H                                         438    2-CH.sub.2 --OCH.sub.3                                                                            F        H                                         439    3-CH.sub.2 --OCH.sub.3                                                                            F        H                                         440    4-CH.sub.2 --OCH.sub.3                                                                            F        H                                         441    2-Me-4-CH.sub.3 --CH(CH.sub.3)--CO                                                                F        H                                         442    2-CH.sub.3 -4-(CH.sub.3 --C═NOCH.sub.3)                                                       F        H                                         443    2-CH.sub.3 -4-(CH.sub.3 --C═NOC.sub.2 H.sub.5)                                                F        H                                         444    2-CH.sub.3 -4-(CH.sub.3 --C═NO-n-C.sub.3 H.sub.7)                                             F        H                                         445    2-CH.sub.3 -4- ( CH.sub.3 --C═NO-i-C.sub.3 H.sub.7)                                           F        H                                         446    2,5-(CH.sub.3)2-4-(CH.sub.3 --C═NOCH.sub.3)                                                   F        H                                         447    2,5-(CH.sub.3)2-4-(CH.sub.3 --C═NOC.sub.2 H.sub.5)                                            F        H                                         448    2,5-(CH.sub.3 -4-(CH.sub.3 --C═NO-n-C.sub.3 H.sub.7)                                          F        H                                         449    2,5-(CH.sub.3)2-4-(CH.sub.3 --C═NO-i-C.sub.3 H.sub.7)                                         F        H                                         450    2-C.sub.6 H.sub.5   F        H                                         451    3-C.sub.6 H.sub.5   F        H                                         452    4-C.sub.6 H.sub.5   F        H                                         453    2-(2'-F--C.sub.6 H.sub.4)                                                                         F        H                                         454    2-CH.sub.3, 5-Br    F        H                                         455    2-CH.sub.3, 6-Br    F        H                                         456    2-Cl, 3-CH.sub.3    F        H                                         457    2-Cl, 4-CH.sub.3    F        H                                         458    2-Cl, 5-CH.sub.3    F        H                                         459    2-F, 3-CH.sub.3     F        H                                         460    2-F, 4-CH.sub.3     F        H                                         461    2-F, 5-CH.sub.3     F        H                                         462    2-Br, 3-CH.sub.3    F        H                                         463    2-Br, 4-CH.sub.3    F        H                                         464    2-Br, 5-CH.sub.3    F        H                                         465    3-CH.sub.3, 4-Cl    F        H                                         466    3-CH.sub.3, 5-Cl    F        H                                         467    3-CH.sub.3, 4-F     F        H                                         468    3-CH.sub.3, 5-F     F        H                                         469    3-CH.sub.3, 4-Br    F        H                                         470    3-CH.sub.3, 5-Br    F        H                                         471    3-F, 4-CH.sub.3     F        H                                         472    3-Cl, 4-CH.sub.3    F        H                                         473    3-Br, 4-CH.sub.3    F        H                                         474    2-Cl, 4,5-(CH.sub.3).sub.2                                                                        F        H                                         475    2-Br, 4,5-(CH.sub.3).sub.2                                                                        F        H                                         476    2-Cl, 3,5-(CH.sub.3).sub.2                                                                        F        H                                         477    2-Br, 3,5-(CH.sub.3).sub.2                                                                        F        H                                         478    2,6-Cl.sub.2, 4-CH.sub.3                                                                          F        H                                         479    2,6-F.sub.2, 4-CH.sub.3                                                                           F        H                                         480    2,6-Br.sub.2, 4-CH.sub.3                                                                          F        H                                         481    2,4-Br.sub.2, 6-CH.sub.3                                                                          F        H                                         482    2,4-F.sub.2, 6-CH.sub.3                                                                           F        H                                         483    2,4-Br.sub.2, 6-CH.sub.3                                                                          F        H                                         484    2,6-(CH.sub.3).sub.2, 4-F                                                                         F        H                                         485    2,6-(CH.sub.3).sub.2, 4-Cl                                                                        F        H                                         486    2,6-(CH.sub.3).sub.2, 4-Br                                                                        F        H                                         487    3,5-(CH.sub.3).sub.2, 4-F                                                                         F        H                                         488    3,5-(CH.sub.3).sub.2, 4-Cl                                                                        F        H                                         489    3,5-(CH.sub.3).sub.2, 4-Br                                                                        F        H                                         490    2-CF.sub.3          F        H                                         491    3-CF.sub.3          F        H                                         492    4-CF.sub.3          F        H                                         493    2-OCF.sub.3         F        H                                         494    3-OCF.sub.3         F        H                                         495    4-OCF.sub.3         F        H                                         496    3-OCH.sub.2 CHF.sub.2                                                                             F        H                                         497    2-NO.sub.2          F        H                                         498    3-NO.sub.2          F        H                                         499    4-NO.sub.2          F        H                                         500    2-CN                F        H                                         501    3-CN                F        H                                         502    4-CN                F        H                                         503    2-CH.sub.3, 3-Cl    F        H                                         504    2-CH.sub.3, 4-Cl    F        H                                         505    2-CH.sub.3, 5-Cl    F        H                                         506    2-CH.sub.3, 6-Cl    F        H                                         507    2-CH.sub.3, 3-F     F        H                                         508    2-CH.sub.3, 4-F     F        H                                         509    2-CH.sub.3, 5-F     F        H                                         510    2-CH.sub.3, 6-F     F        H                                         511    2-CH.sub.3, 3-Br    F        H                                         512    2-CH.sub.3, 4-Br    F        H                                         513    2-Pyridyl-2'        F        H                                         514    3-Pyridyl-3'        F        H                                         515    4-Pyridyl-4'        F        H                                         516    2-CO--CH.sub.3      F        H                                         517    3-CO--CH.sub.3      F        H                                         518    4-CO--CH.sub.3      F        H                                         519    2-C(═N--OCH.sub.3)--CH.sub.3                                                                  F        H                                         520    3-C(═N--OCH.sub.3)--CH.sub.3                                                                  F        H                                         521    4-C(═N--OCH.sub.3)--CH.sub.3                                                                  F        H                                         522    2-F                 Cl       H                                         523    3-F                 Cl       H                                         524    4-F                 Cl       H                                         525    2,4-F.sub.2         Cl       H                                         526    2,4,6-F.sub.3       Cl       H                                         527    2,3,4,5,6-F.sub.5   Cl       H                                         528    2,3-F.sub.2         Cl       H                                         529    2-Cl                Cl       H                                         530    3-Cl                Cl       H                                         531    4-Cl                Cl       H                                         532    2,3-Cl.sub.2        Cl       H                                         533    2,4-Cl.sub.2        Cl       H                                         534    2,5-Cl.sub.2        Cl       H                                         535    2,6-Cl.sub.2        Cl       H                                         536    3,4-Cl.sub.2        Cl       H                                         537    3,5-Cl.sub.2        Cl       H                                         538    2,3,4-Cl.sub.3      Cl       H                                         539    2,3,5-Cl.sub.3      Cl       H                                         540    2,3,6-Cl.sub.3      Cl       H                                         541    2,4,5-Cl.sub.3      Cl       H                                         542    2,4,6-Cl.sub.3      Cl       H                                         543    3,4,5-Cl.sub.3      Cl       H                                         544    2,3,4,6-Cl.sub.4    Cl       H                                         545    2,3,5,6-Cl.sub.4    Cl       H                                         546    2,3,4,5,6-Cl.sub.5  Cl       H                                         547    2-Br                Cl       H                                         548    3-Br                Cl       H                                         549    4-Br                Cl       H                                         550    2,4-Br.sub.2        Cl       H                                         551    2,5-Br.sub.2        Cl       H                                         552    2,6-Br.sub.2        Cl       H                                         553    2,4,6-Br.sub.3      Cl       H                                         554    2,3,4,5,6-Br.sub.5  Cl       H                                         555    2-I                 Cl       H                                         556    3-I                 Cl       H                                         557    4-I                 Cl       H                                         558    2,4-I.sub.2         Cl       H                                         559    2-Cl, 3-F           Cl       H                                         560    2-Cl, 4-F           Cl       H                                         561    2-Cl, 5-F           Cl       H                                         562    2-Cl, 6-F           Cl       H                                         563    2-Cl, 3-Br          Cl       H                                         564    2-Cl, 4-Br          Cl       H                                         565    2-Cl, 5-Br          Cl       H                                         566    2-Cl, 6-Br          Cl       H                                         567    2-Br, 3-Cl          Cl       H                                         568    2-Br, 4-Cl          Cl       H                                         569    2-Br, 5-Cl          Cl       H                                         570    2-Br, 3-F           Cl       H                                         571    2-Br, 4-F           Cl       H                                         572    2-Br, 5-F           Cl       H                                         573    2-Br, 6-F           Cl       H                                         574    2-F, 3-Cl           Cl       H                                         575    2-F, 4-Cl           Cl       H                                         576    2-F, 5-Cl           Cl       H                                         577    3-Cl, 4-F           Cl       H                                         578    3-Cl, 5-F           Cl       H                                         579    3-Cl, 4-Br          Cl       H                                         580    3-Cl, 5-Br          Cl       H                                         581    3-F, 4-Cl           Cl       H                                         582    3-F, 4-Br           Cl       H                                         583    3-Br, 4-Cl          Cl       H                                         584    3-Br, 4-F           Cl       H                                         585    2,6-Cl.sub.2, 4-Br  Cl       H                                         586    2-CH.sub.3          Cl       H                                         587    3-CH.sub.3          Cl       H                                         588    4-CH.sub.3          Cl       H                                         589    2,3-(CH.sub.3).sub.2                                                                              Cl       H                                         590    2,4-(CH.sub.3).sub.2                                                                              Cl       H                                         591    2,5-(CH.sub.3).sub.2                                                                              Cl       H                                         592    2,6-(CH.sub.3).sub.2                                                                              Cl       H                                         593    3,4-(CH.sub.3).sub.2                                                                              Cl       H                                         594    3,5-(CH.sub.3).sub.2                                                                              Cl       H                                         595    2,3,5-(CH.sub.3).sub.3                                                                            Cl       H                                         596    2,3,4-(CH.sub.3).sub.3                                                                            Cl       H                                         597    2,3,6-(CH.sub.3).sub.3                                                                            Cl       H                                         598    2,4,5-(CH.sub.3).sub.3                                                                            Cl       H                                         599    2,4,6-(CH.sub.3).sub.3                                                                            Cl       H                                         600    3,4,5-(CH.sub.3).sub.3                                                                            Cl       H                                         601    2,3,4,6-(CH.sub.3).sub.4                                                                          Cl       H                                         602    2,3,5,6-(CH.sub.3).sub.4                                                                          Cl       H                                         603    2,3,4,5,6-(CH.sub.3).sub.5                                                                        Cl       H                                         604    2-C.sub.2 H.sub.5   Cl       H                                         605    3-C.sub.2 H.sub.5   Cl       H                                         606    4-C.sub.2 H.sub.5   Cl       H                                         607    2,4-(C.sub.2 H.sub.5).sub.5                                                                       Cl       H                                         608    2,6-(C.sub.2 H.sub.5).sub.2                                                                       Cl       H                                         609    3,5-(C.sub.2 H.sub.5).sub.2                                                                       Cl       H                                         610    2,4,6-(C.sub.2 H.sub.5).sub.3                                                                     Cl       H                                         611    2-n-C.sub.3 H.sub.7 Cl       H                                         612    3-n-C.sub.3 H.sub.7 Cl       H                                         613    4-n-C.sub.3 H.sub.7 Cl       H                                         614    2-i-C.sub.3 H.sub.7 Cl       H                                         615    3-i-C.sub.3 H.sub.7 Cl       H                                         616    4-i-C.sub.3 H.sub.7 Cl       H                                         617    2,4-(i-C.sub.3 H.sub.7).sub.2                                                                     Cl       H                                         618    2,6-(i-C.sub.3 H.sub.7).sub.2                                                                     Cl       H                                         619    3,5-(i-C.sub.3 H.sub.7).sub.2                                                                     Cl       H                                         620    2-s-C.sub.4 H.sub.9 Cl       H                                         621    3-s-C.sub.4 H.sub.9 Cl       H                                         622    4-s-C.sub.4 H.sub.9 Cl       H                                         623    2-t-C.sub.4 H.sub.9 Cl       H                                         624    3-t-C.sub.4 H.sub.9 Cl       H                                         625    4-t-C.sub.4 H.sub.9 Cl       H                                         626    4-n-C.sub.9 H.sub.19                                                                              Cl       H                                         627    2-CH.sub.3, 4-t-C.sub.4 H.sub.9                                                                   Cl       H                                         628    2-CH.sub.3, 6-t-C.sub.4 H.sub.9                                                                   Cl       H                                         629    2-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                   Cl       H                                         630    2-CH.sub.3, 5-i-C.sub.3 H.sub.7                                                                   Cl       H                                         631    3-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                   Cl       H                                         632    2-cyclo-C.sub.6 H.sub.11                                                                          Cl       H                                         633    3-cyclo-C.sub.6 H.sub.11                                                                          Cl       H                                         634    4-cyclo-C.sub.6 H.sub.11                                                                          Cl       H                                         635    2-Cl, 4-C.sub.6 H.sub.5                                                                           Cl       H                                         636    2-Br, 4-C.sub.6 H.sub.5                                                                           Cl       H                                         637    2-OCH.sub.3         Cl       H                                         638    3-OCH.sub.3         Cl       H                                         639    4-OCH.sub.3         Cl       H                                         640    2-OC.sub.2 H.sub.5  Cl       H                                         641    3-O--C.sub.2 H.sub.5                                                                              Cl       H                                         642    4-O--C.sub.2 H.sub.5                                                                              Cl       H                                         643    2-O-n-C.sub.3 H.sub.7                                                                             Cl       H                                         644    3-O-n-C.sub.3 H.sub.7                                                                             Cl       H                                         645    4-O-n-C.sub.3 H.sub.7                                                                             Cl       H                                         646    2-O-i-C.sub.3 H.sub.7                                                                             Cl       H                                         647    3-O-i-C.sub.3 H.sub.7                                                                             Cl       H                                         648    4-O-i-C.sub.3 H.sub.7                                                                             Cl       H                                         649    2-O-n-C.sub.6 H.sub.13                                                                            Cl       H                                         650    3-O-n-C.sub.6 H.sub.13                                                                            Cl       H                                         651    4-O-n-C.sub.6 H.sub.13                                                                            Cl       H                                         652    2-O--CH.sub.2 C.sub.6 H.sub.5                                                                     Cl       H                                         653    3-O--CH.sub.2 C.sub.6 H.sub.5                                                                     Cl       H                                         654    4-O--CH.sub.2 C.sub.6 H.sub.5                                                                     Cl       H                                         655    2-O--(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                             Cl       H                                         656    4-O--(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                             Cl       H                                         657    2,3-(OCH.sub.3).sub.2                                                                             Cl       H                                         658    2,4-(OCH.sub.3).sub.2                                                                             Cl       H                                         659    2,5-(OCH.sub.3).sub.2                                                                             Cl       H                                         660    2,6-(OCH.sub.3).sub.2                                                                             Cl       H                                         661    3,4-(OCH.sub.3).sub.2                                                                             Cl       H                                         662    3,5-(OCH.sub.3).sub.2                                                                             Cl       H                                         663    2-O-t-C.sub.4 H.sub.9                                                                             Cl       H                                         664    3-O-t-C.sub.4 H.sub.9                                                                             Cl       H                                         665    4-O-t-C.sub.4 H.sub.9                                                                             Cl       H                                         666    3-(3'-Cl--C.sub.6 H.sub.4)                                                                        Cl       H                                         667    4-(4'-CH.sub.3 --C.sub.6 H.sub.4)                                                                 Cl       H                                         668    2-O--C.sub.6 H.sub.5                                                                              Cl       H                                         669    3-O--C.sub.6 H.sub.5                                                                              Cl       H                                         670    4-O--C.sub.6 H.sub.5                                                                              Cl       H                                         671    2-O-(2'-F--C.sub.6 H.sub.4)                                                                       Cl       H                                         672    3-O-(3'-Cl--C.sub.6 H.sub.4)                                                                      Cl       H                                         673    4-O-(4'-CH.sub.3 --C.sub.6 H.sub.4)                                                               Cl       H                                         674    2,3,6-(CH.sub.3).sub.3, 4-F                                                                       Cl       H                                         675    2,3,6-(CH.sub.3).sub.3, 4-Cl                                                                      Cl       H                                         676    2,3,6-(CH.sub.3).sub.3, 4-Br                                                                      Cl       H                                         677    2,4-(CH.sub.3).sub.2, 6-F                                                                         Cl       H                                         678    2,4-(CH.sub.3).sub.2, 6-Cl                                                                        Cl       H                                         679    2,4-(CH.sub.3).sub.2, 6-Br                                                                        Cl       H                                         680    2-i-CH.sub.3 H.sub.1, 4-Cl, 5-CH.sub.3                                                            Cl       H                                         681    2-Cl, 4-NO.sub.2    Cl       H                                         682    2-NO.sub.2, 4-Cl    Cl       H                                         683    2-OCH.sub.3, 5-NO.sub.2                                                                           Cl       H                                         684    2,4-Cl.sub.2, 5-NO.sub.2                                                                          Cl       H                                         685    2,4-Cl.sub.2, 6-NO.sub.2                                                                          Cl       H                                         686    2,6-Cl.sub.2, 4-NO.sub.2                                                                          Cl       H                                         687    2,6-Br.sub.2, 4-NO.sub.2                                                                          Cl       H                                         688    2,6-I.sub.2, 4-NO.sub.2                                                                           Cl       H                                         689    2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl                                                             Cl       H                                         690    2-CO.sub.2 CH.sub.3 Cl       H                                         691    3-CO.sub.2 CH.sub.3 Cl       H                                         692    4-CO.sub.2 CH.sub.3 Cl       H                                         693    2-CH.sub.2 --OCH.sub.3                                                                            Cl       H                                         694    3-CH.sub.2 --OCH.sub.3                                                                            Cl       H                                         695    4-CH.sub.2 --OCH.sub.3                                                                            Cl       H                                         696    2-Me-4-CH.sub.3 --CH(CH.sub.3)--CO                                                                Cl       H                                         697    2-CH.sub.3 -4-(CH.sub.3 --C═NOCH.sub.3)                                                       Cl       H                                         698    2-CH.sub.3 -4-(CH.sub.3 --C═NOC.sub.2 H.sub.5)                                                Cl       H                                         699    2-CH.sub.3 -4-(CH.sub.3 --C═NO-n-C.sub.3 H.sub.7)                                             Cl       H                                         700    2-CH.sub.3 -4-(CH.sub.3 --C═NO-i-C.sub.3 H.sub.7)                                             Cl       H                                         701    2,5-(CH.sub.3)2-4-(CH.sub.3 --C═NOCH.sub.3)                                                   Cl       H                                         702    2,5-(CH.sub.3)2-4-(CH.sub.3 --C═NOC.sub.2 H.sub.5)                                            Cl       H                                         703    2,5-(CH.sub.3 -4-(CH.sub.3 --C═NO-n-C.sub.3 H.sub.7)                                          Cl       H                                         704    2,5-(CH.sub.3).sub.2 -4-(CH.sub.3 --C═NO-i-C.sub.3 H.sub.7)                                   Cl       H                                         705    2-C.sub.6 H.sub.5   Cl       H                                         706    3-C.sub.6 H.sub.5   Cl       H                                         707    4-C.sub.6 H.sub.5   Cl       H                                         708    2-(2'-F--C.sub.6 H.sub.4)                                                                         Cl       H                                         709    2-CH.sub.3, 5-Br    Cl       H                                         710    2-CH.sub.3, 6-Br    Cl       H                                         711    2-Cl, 3-CH.sub.3    Cl       H                                         712    2-Cl, 4-CH.sub.3    Cl       H                                         713    2-Cl, 5-CH.sub.3    Cl       H                                         714    2-F, 3-CH.sub.3     Cl       H                                         715    2-F, 4-CH.sub.3     Cl       H                                         716    2-F, 5-CH.sub.3     Cl       H                                         717    2-Br, 3-CH.sub.3    Cl       H                                         716    2-Br, 4-CH.sub.3    Cl       H                                         719    2-Br, 5-CH.sub.3    Cl       H                                         720    3-CH.sub.3, 4-Cl    Cl       H                                         721    3-CH.sub.3, 5-Cl    Cl       H                                         722    3-CH.sub.3, 4-F     Cl       H                                         723    3-CH.sub.3, 5-F     Cl       H                                         724    3-CH.sub.3, 4-Br    Cl       H                                         725    3-CH.sub.3, 5-Br    Cl       H                                         726    3-F, 4-CH.sub.3     Cl       H                                         727    3-Cl, 4-CH.sub.3    Cl       H                                         728    3-Br, 4-CH.sub.3    Cl       H                                         729    2-Cl, 4,5-(CH.sub.3).sub.2                                                                        Cl       H                                         730    2-Br, 4,5-(CH.sub.3).sub.2                                                                        Cl       H                                         731    2-Cl, 3,5-(CH.sub.3).sub.2                                                                        Cl       H                                         732    2-Br, 3,5-(CH.sub.3).sub.2                                                                        Cl       H                                         733    2,6-Cl.sub.2, 4-CH.sub.3                                                                          Cl       H                                         734    2,6-F.sub.2, 4-CH.sub.3                                                                           Cl       H                                         735    2,6-Br.sub.2, 4-CH.sub.3                                                                          Cl       H                                         736    2,4-Br.sub.2, 6-CH.sub.3                                                                          Cl       H                                         737    2,4-F.sub.2, 6-CH.sub.3                                                                           Cl       H                                         738    2,4-Br.sub.2, 6-CH.sub.3                                                                          Cl       H                                         739    2,6-(CH.sub.3).sub.2, 4-F                                                                         Cl       H                                         740    2,6-(CH.sub.3).sub.2, 4-Cl                                                                        Cl       H                                         741    2,6-(CH.sub.3).sub.2, 4-Br                                                                        Cl       H                                         742    3,5-(CH.sub.3).sub.2, 4-F                                                                         Cl       H                                         743    3,5-(CH.sub.3).sub.2, 4-Cl                                                                        Cl       H                                         744    3,5-(CH.sub.3).sub.2, 4-Br                                                                        Cl       H                                         745    2-CF.sub.3          Cl       H                                         746    3-CF.sub.3          Cl       H                                         747    4-CF.sub.3          Cl       H                                         748    2-OCF.sub.3         Cl       H                                         749    3-OCF.sub.3         Cl       H                                         750    4-OCF.sub.3         Cl       H                                         751    3-OCH.sub.2 CHF.sub.2                                                                             Cl       H                                         752    2-NO.sub.2          Cl       H                                         753    3-NO.sub.2          Cl       H                                         754    4-NO.sub.2          Cl       H                                         755    2-CN                Cl       H                                         756    3-CN                Cl       H                                         757    4-CN                Cl       H                                         758    2-CH.sub.3, 3-Cl    Cl       H                                         759    2-CH.sub.3, 4-Cl    Cl       H                                         760    2-CH.sub.3, 5-Cl    Cl       H                                         761    2-CH.sub.3, 6-Cl    Cl       H                                         762    2-CH.sub.3, 3-F     Cl       H                                         763    2-CH.sub.3, 4-F     Cl       H                                         764    2-CH.sub.3, 5-F     Cl       H                                         765    2-CH.sub.3, 6-F     Cl       H                                         766    2-CH.sub.3, 3-Br    Cl       H                                         767    2-CH.sub.3, 4-Br    Cl       H                                         768    2-Pyridyl-2'        Cl       H                                         769    3-Pyridyl-3'        Cl       H                                         770    4-Pyridyl-4'        Cl       H                                         771    2-CO--CH.sub.3      Cl       H                                         772    3-CO--CH.sub.3      Cl       H                                         773    4-CO--CH.sub.3      Cl       H                                         774    2-C(═N--OCH.sub.3)--CH.sub.3                                                                  Cl       H                                         775    3-C(═N--OCH.sub.3)--CH.sub.3                                                                  Cl       H                                         776    4-C(═N--OCH.sub.3)--CH.sub.3                                                                  Cl       H                                         777    2-F                 CN       H                                         778    3-F                 CN       H                                         779    4-F                 CN       H                                         780    2,4-F.sub.2         CN       H                                         781    2,4,6-F.sub.3       CN       H                                         782    2,3,4,5,6-F.sub.5   CN       H                                         783    2,3-F.sub.2         CN       H                                         784    2-Cl                CN       H                                         785    3-Cl                CN       H                                         786    4-Cl                CN       H                                         787    2,3-Cl.sub.2        CN       H                                         788    2,4-Cl.sub.2        CN       H                                         789    2,5-Cl.sub.2        CN       H                                         790    2,6-Cl.sub.2        CN       H                                         791    3,4-Cl.sub.2        CN       H                                         792    3,5-Cl.sub.2        CN       H                                         793    2,3,4-Cl.sub.3      CN       H                                         794    2,3,5-Cl.sub.3      CN       H                                         795    2,3,6-Cl.sub.3      CN       H                                         796    2,4,5-Cl.sub.3      CN       H                                         797    2,4,6-Cl.sub.3      CN       H                                         798    3,4,5-Cl.sub.3      CN       H                                         799    2,3,4,6-Cl.sub.4    CN       H                                         800    2,3,5,6-Cl.sub.4    CN       H                                         801    2,3,4,5,6-Cl.sub.5  CN       H                                         802    2-Br                CN       H                                         803    3-Br                CN       H                                         804    4-Br                CN       H                                         805    2,4-Br.sub.2        CN       H                                         806    2,5-Br.sub.2        CN       H                                         807    2,6-Br.sub.2        CN       H                                         808    2,4,6-Br.sub.3      CN       H                                         809    2,3,4,5,6-Br.sub.5  CN       H                                         810    2-I                 CN       H                                         811    3-I                 CN       H                                         812    4-I                 CN       H                                         813    2,4-I.sub.2         CN       H                                         814    2-Cl, 3-F           CN       H                                         815    2-Cl, 4-F           CN       H                                         816    2-Cl, 5-F           CN       H                                         817    2-Cl, 6-F           CN       H                                         818    2-Cl, 3-Br          CN       H                                         819    2-Cl, 4-Br          CN       H                                         820    2-Cl, 5-Br          CN       H                                         821    2-Cl, 6-Br          CN       H                                         822    2-Br, 3-Cl          CN       H                                         823    2-Br, 4-Cl          CN       H                                         824    2-Br, 5-Cl          CN       H                                         625    2-Br, 3-F           CN       H                                         826    2-Br, 4-F           CN       H                                         827    2-Br, 5-F           CN       H                                         828    2-Br, 6-F           CN       H                                         829    2-F, 3-Cl           CN       H                                         830    2-F, 4-Cl           CN       H                                         831    2-F, 5-Cl           CN       H                                         832    3-Cl, 4-F           CN       H                                         833    3-Cl, 5-F           CN       H                                         834    3-Cl, 4-Br          CN       H                                         835    3-Cl, 5-Br          CN       H                                         836    3-F, 4-Cl           CN       H                                         837    3-F, 4-Br           CN       H                                         838    3-Br, 4-Cl          CN       H                                         839    3-Br, 4-F           CN       H                                         840    2,6-Cl.sub.2, 4-Br  CN       H                                         841    2-CH.sub.3          CN       H                                         842    3-CH.sub.3          CN       H                                         843    4-CH.sub.3          CN       H                                         844    2,3-(CH.sub.3).sub.2                                                                              CN       H                                         845    2,4-(CH.sub.3).sub.2                                                                              CN       H                                         846    2,5-(CH.sub.3).sub.2                                                                              CN       H                                         847    2,6-(CH.sub.3).sub.2                                                                              CN       H                                         848    3,4-(CH.sub.3).sub.2                                                                              CN       H                                         849    3,5-(CH.sub.3).sub.2                                                                              CN       H                                         850    2,3,5-(CH.sub.3).sub.3                                                                            CN       H                                         851    2,3,4-(CH.sub.3).sub.3                                                                            CN       H                                         852    2,3,6-(CH.sub.3).sub.3                                                                            CN       H                                         853    2,4,5-(CH.sub.3).sub.3                                                                            CN       H                                         854    2,4,6-(CH.sub.3).sub.3                                                                            CN       H                                         855    3,4,5-(CH.sub.3).sub.3                                                                            CN       H                                         856    2,3,4,6-(CH.sub.3).sub.4                                                                          CN       H                                         857    2,3,5,6-(CH.sub.3).sub.4                                                                          CN       H                                         858    2,3,4,5,6-(CH.sub.3).sub.5                                                                        CN       H                                         859    2-C.sub.2 H.sub.5   CN       H                                         860    3-C.sub.2 H.sub.5   CN       H                                         861    4-C.sub.2 H.sub.5   CN       H                                         862    2,4-(C.sub.2 H.sub.5).sub.5                                                                       CN       H                                         863    2,6-(C.sub.2 H.sub.5).sub.2                                                                       CN       H                                         864    3,5-(C.sub.2 H.sub.5).sub.2                                                                       CN       H                                         865    2,4,6-(C.sub.2 H.sub.5).sub.3                                                                     CN       H                                         866    2-n-C.sub.3 H.sub.7 CN       H                                         867    3-n-C.sub.3 H.sub.7 CN       H                                         868    4-n-C.sub.3 H.sub.7 CN       H                                         869    2-i-C.sub.3 H.sub.7 CN       H                                         870    3-i-C.sub.3 H.sub.7 CN       H                                         871    4-i-C.sub.3 H.sub.7 CN       H                                         872    2,4-(i-C.sub.3 H.sub.7).sub.2                                                                     CN       H                                         873    2,6-(i-C.sub.3 H.sub.7).sub.2                                                                     CN       H                                         874    3,5-(i-C.sub.3 H.sub.7).sub.2                                                                     CN       H                                         875    2-s-C.sub.4 H.sub.9 CN       H                                         876    3-s-C.sub.4 H.sub.9 CN       H                                         877    4-s-C.sub.4 H.sub.9 CN       H                                         878    2-t-C.sub.4 H.sub.9 CN       H                                         879    3-t-C.sub.4 H.sub.9 CN       H                                         880    4-t-C.sub.4 H.sub.9 CN       H                                         881    4-n-C.sub.9 H.sub.19                                                                              CN       H                                         882    2-CH.sub.3, 4-t-C.sub.4 H.sub.9                                                                   CN       H                                         883    2-CH.sub.3, 6-t-C.sub.4 H.sub.9                                                                   CN       H                                         884    2-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                   CN       H                                         885    2-CH.sub.3, 5-i-C.sub.3 H.sub.7                                                                   CN       H                                         886    3-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                   CN       H                                         887    2-cyclo-C.sub.6 H.sub.11                                                                          CN       H                                         888    3-cyclo-C.sub.6 H.sub.11                                                                          CN       H                                         889    4-cyclo-C.sub.6 H.sub.11                                                                          CN       H                                         890    2-Cl, 4-C.sub.6 H.sub.5                                                                           CN       H                                         891    2-Br, 4-C.sub.6 H.sub.5                                                                           CN       H                                         892    2-OCH.sub.3         CN       H                                         893    3-OCH.sub.3         CN       H                                         894    4-OCH.sub.3         CN       H                                         895    2-OC.sub.2 H.sub.5  CN       H                                         896    3-O--C.sub.2 H.sub.5                                                                              CN       H                                         897    4-O--C.sub.2 H.sub.5                                                                              CN       H                                         898    2-O-n-C.sub.3 H.sub.7                                                                             CN       H                                         899    3-O-n-C.sub.3 H.sub.7                                                                             CN       H                                         900    4-O-n-C.sub.3 H.sub.7                                                                             CN       H                                         901    2-O-i-C.sub.3 H.sub.7                                                                             CN       H                                         902    3-O-i-C.sub.3 H.sub.7                                                                             CN       H                                         903    4-O-i-C.sub.3 H.sub.7                                                                             CN       H                                         904    2-O-n-C.sub.6 H.sub.13                                                                            CN       H                                         905    3-O-n-C.sub.6 H.sub.13                                                                            CN       H                                         906    4-O-n-C.sub.6 H.sub.13                                                                            CN       H                                         907    2-O--CH.sub.2 C.sub.6 H.sub.5                                                                     CN       H                                         908    3-O--CH.sub.2 C.sub.6 H.sub.5                                                                     CN       H                                         909    4-O--CH.sub.2 C.sub.6 H.sub.5                                                                     CN       H                                         910    2-O--(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                             CN       H                                         911    4-O--(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                             CN       H                                         912    2,3-(OCH.sub.3).sub.2                                                                             CN       H                                         913    2,4-(OCH.sub.3).sub.2                                                                             CN       H                                         914    2,5-(OCH.sub.3).sub.2                                                                             CN       H                                         915    2,6-(OCH.sub.3).sub.2                                                                             CN       H                                         916    3,4-(OCH.sub.3).sub.2                                                                             CN       H                                         917    3,5-(OCH.sub.3).sub.2                                                                             CN       H                                         918    2-O-t-C.sub.4 H.sub.9                                                                             CN       H                                         919    3-O-t-C.sub.4 H.sub.9                                                                             CN       H                                         920    4-O-t-C.sub.4 H.sub.9                                                                             CN       H                                         921    3-(3'-Cl--C.sub.6 H.sub.4)                                                                        CN       H                                         922    4-(4'-CH.sub.3 --C.sub.6 H.sub.4)                                                                 CN       H                                         923    2-O--C.sub.6 H.sub.5                                                                              CN       H                                         924    3-O--C.sub.6 H.sub.5                                                                              CN       H                                         925    4-O--C.sub.6 H.sub.5                                                                              CN       H                                         926    2-O-(2'-F--C.sub.6 H.sub.4)                                                                       CN       H                                         927    3-O-(3'-Cl--C.sub.6 H.sub.4)                                                                      CN       H                                         928    4-O-(4'-CH.sub.3 --C.sub.6 H.sub.4)                                                               CN       H                                         929    2,3,6-(CH.sub.3).sub.3, 4-F                                                                       CN       H                                         930    2,3,6-(CH.sub.3).sub.3, 4-Cl                                                                      CN       H                                         931    2,3,6-(CH.sub.3).sub.3, 4-Br                                                                      CN       H                                         932    2,4-(CH.sub.3).sub.2, 6-F                                                                         CN       H                                         933    2,4-(CH.sub.3).sub.2, 6-Cl                                                                        CN       H                                         934    2,4-(CH.sub.3).sub.2, 6-Br                                                                        CN       H                                         935    2-i-CH.sub.3 H.sub.1, 4-Cl, 5-CH.sub.3                                                            CN       H                                         936    2-Cl, 4-NO.sub.2    CN       H                                         937    2-NO.sub.2, 4-Cl    CN       H                                         938    2-OCH.sub.3, 5-NO.sub.2                                                                           CN       H                                         939    2,4-Cl.sub.2, 5-NO.sub.2                                                                          CN       H                                         940    2,4-Cl.sub.2, 6-NO.sub.2                                                                          CN       H                                         941    2,6-Cl.sub.2, 4-NO.sub.2                                                                          CN       H                                         942    2,6-Br.sub.2, 4-NO.sub.2                                                                          CN       H                                         943    2,6-I.sub.2, 4-NO.sub.2                                                                           CN       H                                         944    2-CH.sub.3, 5-i-CH.sub.3 H.sub.7, 4-Cl                                                            CN       H                                         945    2-CO.sub.2 CH.sub.3 CN       H                                         946    3-CO.sub.2 CH.sub.3 CN       H                                         947    4-CO.sub.2 CH.sub.3 CN       H                                         948    2-CH.sub.2 --OCH.sub.3                                                                            CN       H                                         949    3-CH.sub.2 --OCH.sub.3                                                                            CN       H                                         950    4-CH.sub.2 --OCH.sub.3                                                                            CN       H                                         951    2-Me-4-CH.sub.3 --CH(CH.sub.3)--CO                                                                CN       H                                         952    2-CH.sub.3 -4-(CH.sub.3 --C═NOCH.sub.3)                                                       CN       H                                         953    2-CH.sub.3 -4-(CH.sub.3 --C═NOC.sub.2 H.sub.5)                                                CN       H                                         954    2-CH.sub.3 -4-(CH.sub.3 --C═NO-n-C.sub.3 H.sub.7)                                             CN       H                                         955    2-CH.sub.3 -4-(CH.sub.3 --C═NO-i-C.sub.3 H.sub.7)                                             CN       H                                         956    2,5-(CH.sub.3).sub.2 -4-(CH.sub.3 --C═NOCH.sub.3)                                             CN       H                                         957    2,5-(CH.sub.3).sub.2 -4-(CH.sub.3 --C═NOC.sub.2 H.sub.5)                                      CN       H                                         958    2,5-(CH.sub.3 -4-(CH.sub.3 --C═NO-n-C.sub.3 H.sub.7)                                          CN       H                                         959    2,5-(CH.sub.3).sub.2 -4-(CH.sub.3 --C═NO-i-C.sub.3 H.sub.7)                                   CN       H                                         960    2-C.sub.6 H.sub.5   CN       H                                         961    3-C.sub.6 H.sub.5   CN       H                                         962    4-C.sub.6 H.sub.5   CN       H                                         963    2-(2'-F--C.sub.6 H.sub.4)                                                                         CN       H                                         964    2-CH.sub.3, 5-Br    CN       H                                         965    2-CH.sub.3, 6-Br    CN       H                                         966    2-Cl, 3-CH.sub.3    CN       H                                         967    2-Cl, 4-CH.sub.3    CN       H                                         968    2-Cl, 5-CH.sub.3    CN       H                                         969    2-F, 3-CH.sub.3     CN       H                                         970    2-F, 4-CH.sub.3     CN       H                                         971    2-F, 5-CH.sub.3     CN       H                                         972    2-Br, 3-CH.sub.3    CN       H                                         973    2-Br, 4-CH.sub.3    CN       H                                         974    2-Br, 5-CH.sub.3    CN       H                                         975    3-CH.sub.3, 4-Cl    CN       H                                         976    3-CH.sub.3, 5-Cl    CN       H                                         977    3-CH.sub.3, 4-F     CN       H                                         978    3-CH.sub.3, 5-F     CN       H                                         979    3-CH.sub.3, 4-Br    CN       H                                         980    3-CH.sub.3, 5-Br    CN       H                                         981    3-F, 4-CH.sub.3     CN       H                                         982    3-Cl, 4-CH.sub.3    CN       H                                         983    3-Br, 4-CH.sub.3    CN       H                                         984    2-Cl, 4,5-(CH.sub.3).sub.2                                                                        CN       H                                         985    2-Br, 4,5-(CH.sub.3).sub.2                                                                        CN       H                                         986    2-Cl, 3,5-(CH.sub.3).sub.2                                                                        CN       H                                         987    2-Br, 3,5-(CH.sub.3).sub.2                                                                        CN       H                                         988    2,6-Cl.sub.2, 4-CH.sub.3                                                                          CN       H                                         989    2,6-F.sub.2, 4-CH.sub.3                                                                           CN       H                                         990    2,6-Br.sub.2, 4-CH.sub.3                                                                          CN       H                                         991    2,4-Br.sub.2, 6-CH.sub.3                                                                          CN       H                                         992    2,4-F.sub.2, 6-CH.sub.3                                                                           CN       H                                         993    2,4-Br.sub.2, 6-CH.sub.3                                                                          CN       H                                         994    2,6-(CH.sub.3).sub.2, 4-F                                                                         CN       H                                         995    2,6-(CH.sub.3).sub.2, 4-Cl                                                                        CN       H                                         996    2,6-(CH.sub.3).sub.2, 4-Br                                                                        CN       H                                         997    3,5-(CH.sub.3).sub.2, 4-F                                                                         CN       H                                         998    3,5-(CH.sub.3).sub.2, 4-Cl                                                                        CN       H                                         999    3,5-(CH.sub.3).sub.2, 4-Br                                                                        CN       H                                         1000   2-CF.sub.3          CN       H                                         1001   3-CF.sub.3          CN       H                                         1002   4-CF.sub.3          CN       H                                         1003   2-OCF.sub.3         CN       H                                         1004   3-OCF.sub.3         CN       H                                         1005   4-OCF.sub.3         CN       H                                         1006   3-OCH.sub.2 CHF.sub.2                                                                             CN       H                                         1007   2-NO.sub.2          CN       H                                         1008   3-NO.sub.2          CN       H                                         1009   4-NO.sub.2          CN       H                                         1010   2-CN                CN       H                                         1011   3-CN                CN       H                                         1012   4-CN                CN       H                                         1013   2-CH.sub.3, 3-Cl    CN       H                                         1014   2-CH.sub.3, 4-Cl    CN       H                                         1015   2-CH.sub.3, 5-Cl    CN       H                                         1016   2-CH.sub.3, 6-Cl    CN       H                                         1017   2-CH.sub.3, 3-F     CN       H                                         1018   2-CH.sub.3, 4-F     CN       H                                         1019   2-CH.sub.3, 5-F     CN       H                                         1020   2-CH.sub.3, 6-F     CN       H                                         1021   2-CH.sub.3, 3-Br    CN       H                                         1022   2-CH.sub.3, 4-Br    CN       H                                         1023   2-Pyridyl-2'        CN       H                                         1024   3-Pyridyl-3'        CN       H                                         1025   4-Pyridyl-4'        CN       H                                         1026   2-CO--CH.sub.3      CN       H                                         1027   3-CO--CH.sub.3      CN       H                                         1028   4-CO--CH.sub.3      CN       H                                         1029   2-C(═N--OCH.sub.3)--CH.sub.3                                                                  CN       H                                         1030   3-C(═N--OCH.sub.3)--CH.sub.3                                                                  CN       H                                         1031   4-C(═N--OCH.sub.3)--CH.sub.3                                                                  CN       H                                         1032   2-F                 OCH.sub.3                                                                              H                                         1033   3-F                 OCH.sub.3                                                                              H                                         1034   4-F                 OCH.sub.3                                                                              H                                         1035   2,4-F.sub.2         OCH.sub.3                                                                              H                                         1036   2,4,6-F.sub.3       OCH.sub.3                                                                              H                                         1037   2,3,4,5,6-F.sub.5   OCH.sub.3                                                                              H                                         1038   2,3-F.sub.2         OCH.sub.3                                                                              H                                         1039   2-Cl                OCH.sub.3                                                                              H                                         1040   3-Cl                OCH.sub.3                                                                              H                                         1041   4-Cl                OCH.sub.3                                                                              H                                         1042   2,3-Cl.sub.2        OCH.sub.3                                                                              H                                         1043   2,4-Cl.sub.2        OCH.sub.3                                                                              H                                         1044   2,5-Cl.sub.2        OCH.sub.3                                                                              H                                         1045   2,6-Cl.sub.2        OCH.sub.3                                                                              H                                         1046   3,4-Cl.sub.2        OCH.sub.3                                                                              H                                         1047   3,5-Cl.sub.2        OCH.sub.3                                                                              H                                         1048   2,3,4-Cl.sub.3      OCH.sub.3                                                                              H                                         1049   2,3,5-Cl.sub.3      OCH.sub.3                                                                              H                                         1050   2,3,6-Cl.sub.3      OCH.sub.3                                                                              H                                         1051   2,4,5-Cl.sub.3      OCH.sub.3                                                                              H                                         1052   2,4,6-Cl.sub.3      OCH.sub.3                                                                              H                                         1053   3,4,5-Cl.sub.3      OCH.sub.3                                                                              H                                         1054   2,3,4,6-Cl.sub.4    OCH.sub.3                                                                              H                                         1055   2,3,5,6-Cl.sub.4    OCH.sub.3                                                                              H                                         1056   2,3,4,5,6-Cl.sub.5  OCH.sub.3                                                                              H                                         1057   2-Br                OCH.sub.3                                                                              H                                         1058   3-Br                OCH.sub.3                                                                              H                                         1059   4-Br                OCH.sub.3                                                                              H                                         1060   2,4-Br.sub.2        OCH.sub.3                                                                              H                                         1061   2,5-Br.sub.2        OCH.sub.3                                                                              H                                         1062   2,6-Br.sub.2        OCH.sub.3                                                                              H                                         1063   2,4,6-Br.sub.3      OCH.sub.3                                                                              H                                         1064   2,3,4,5,6-Br.sub.5  OCH.sub.3                                                                              H                                         1065   2-I                 OCH.sub.3                                                                              H                                         1066   3-I                 OCH.sub.3                                                                              H                                         1067   4-I                 OCH.sub.3                                                                              H                                         1068   2,4-I.sub.2         OCH.sub.3                                                                              H                                         1069   2-Cl, 3-F           OCH.sub.3                                                                              H                                         1070   2-Cl, 4-F           OCH.sub.3                                                                              H                                         1071   2-Cl, 5-F           OCH.sub.3                                                                              H                                         1072   2-Cl, 6-F           OCH.sub.3                                                                              H                                         1073   2-Cl, 3-Br          OCH.sub.3                                                                              H                                         1074   2-Cl, 4-Br          OCH.sub.3                                                                              H                                         1075   2-Cl, 5-Br          OCH.sub.3                                                                              H                                         1076   2-Cl, 6-Br          OCH.sub.3                                                                              H                                         1077   2-Br, 3-Cl          OCH.sub.3                                                                              H                                         1078   2-Br, 4-Cl          OCH.sub.3                                                                              H                                         1079   2-Br, 5-Cl          OCH.sub.3                                                                              H                                         1080   2-Br, 3-F           OCH.sub.3                                                                              H                                         1081   2-Br, 4-F           OCH.sub.3                                                                              H                                         1082   2-Br, 5-F           OCH.sub.3                                                                              H                                         1083   2-Br, 6-F           OCH.sub.3                                                                              H                                         1084   2-F, 3-Cl           OCH.sub.3                                                                              H                                         1085   2-F, 4-Cl           OCH.sub.3                                                                              H                                         1086   2-F, 5-Cl           OCH.sub.3                                                                              H                                         1087   3-Cl, 4-F           OCH.sub.3                                                                              H                                         1088   3-Cl, 5-F           OCH.sub.3                                                                              H                                         1089   3-Cl, 4-Br          OCH.sub.3                                                                              H                                         1090   3-Cl, 5-Br          OCH.sub.3                                                                              H                                         1091   3-F, 4-Cl           OCH.sub.3                                                                              H                                         1092   3-F, 4-Br           OCH.sub.3                                                                              H                                         1093   3-Br, 4-Cl          OCH.sub.3                                                                              H                                         1094   3-Br, 4-F           OCH.sub.3                                                                              H                                         1095   2,6-Cl.sub.2, 4-Br  OCH.sub.3                                                                              H                                         1096   2-CH.sub.3          OCH.sub.3                                                                              H                                         1097   3-CH.sub.3          OCH.sub.3                                                                              H                                         1098   4-CH.sub.3          OCH.sub.3                                                                              H                                         1099   2,3-(CH.sub.3).sub.2                                                                              OCH.sub.3                                                                              H                                         1100   2,4-(CH.sub.3).sub.2                                                                              OCH.sub.3                                                                              H                                         1101   2,5-(CH.sub.3).sub.2                                                                              OCH.sub.3                                                                              H                                         1102   2,6-(CH.sub.3).sub.2                                                                              OCH.sub.3                                                                              H                                         1103   3,4-(CH.sub.3).sub.2                                                                              OCH.sub.3                                                                              H                                         1104   3,5-(CH.sub.3).sub.2                                                                              OCH.sub.3                                                                              H                                         1105   2,3,5-(CH.sub.3).sub.3                                                                            OCH.sub.3                                                                              H                                         1106   2,3,4-(CH.sub.3).sub.3                                                                            OCH.sub.3                                                                              H                                         1107   2,3,6-(CH.sub.3).sub.3                                                                            OCH.sub.3                                                                              H                                         1108   2,4,5-(CH.sub.3).sub.3                                                                            OCH.sub.3                                                                              H                                         1109   2,4,6-(CH.sub.3).sub.3                                                                            OCH.sub.3                                                                              H                                         1110   3,4,5-(CH.sub.3).sub.3                                                                            OCH.sub.3                                                                              H                                         1111   2,3,4,6-(CH.sub.3).sub.4                                                                          OCH.sub.3                                                                              H                                         1112   2,3,5,6-(CH.sub.3).sub.4                                                                          OCH.sub.3                                                                              H                                         1113   2,3,4,5,6-(CH.sub.3).sub.5                                                                        OCH.sub.3                                                                              H                                         1114   2-C.sub.2 H.sub.5   OCH.sub.3                                                                              H                                         1115   3-C.sub.2 H.sub.5   OCH.sub.3                                                                              H                                         1116   4-C.sub.2 H.sub.5   OCH.sub.3                                                                              H                                         1117   2,4-(C.sub.2 H.sub.5).sub.5                                                                       OCH.sub.3                                                                              H                                         1118   2,6-(C.sub.2 H.sub.5).sub.2                                                                       OCH.sub.3                                                                              H                                         1119   3,5-(C.sub.2 H.sub.5).sub.2                                                                       OCH.sub.3                                                                              H                                         1120   2,4,6-(C.sub.2 H.sub.5).sub.3                                                                     OCH.sub.3                                                                              H                                         1121   2-n-C.sub.3 H.sub.7 OCH.sub.3                                                                              H                                         1122   3-n-C.sub.3 H.sub.7 OCH.sub.3                                                                              H                                         1123   4-n-C.sub.3 H.sub.7 OCH.sub.3                                                                              H                                         1124   2-i-C.sub.3 H.sub.7 OCH.sub.3                                                                              H                                         1125   3-i-C.sub.3 H.sub.7 OCH.sub.3                                                                              H                                         1126   4-i-C.sub.3 H.sub.7 OCH.sub.3                                                                              H                                         1127   2,4-(i-C.sub.3 H.sub.7).sub.2                                                                     OCH.sub.3                                                                              H                                         1128   2,6-(i-C.sub.3 H.sub.7).sub.2                                                                     OCH.sub.3                                                                              H                                         1129   3,5-(i-C.sub.3 H.sub.7).sub.2                                                                     OCH.sub.3                                                                              H                                         1130   2-s-C.sub.4 H.sub.9 OCH.sub.3                                                                              H                                         1131   3-s-C.sub.4 H.sub.9 OCH.sub.3                                                                              H                                         1132   4-s-C.sub.4 H.sub.9 OCH.sub.3                                                                              H                                         1133   2-t-C.sub.4 H.sub.9 OCH.sub.3                                                                              H                                         1134   3-t-C.sub.4 H.sub.9 OCH.sub.3                                                                              H                                         1135   4-t-C.sub.4 H.sub.9 OCH.sub.3                                                                              H                                         1136   4-n-C.sub.9 H.sub.19                                                                              OCH.sub.3                                                                              H                                         1137   2-CH.sub.3, 4-t-C.sub.4 H.sub.9                                                                   OCH.sub.3                                                                              H                                         1138   2-CH.sub.3, 6-t-C.sub.4 H.sub.9                                                                   OCH.sub.3                                                                              H                                         1139   2-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                   OCH.sub.3                                                                              H                                         1140   2-CH.sub.3, 5-i-C.sub.3 H.sub.7                                                                   OCH.sub.3                                                                              H                                         1141   3-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                   OCH.sub.3                                                                              H                                         1142   2-cyclo-C.sub.6 H.sub.11                                                                          OCH.sub.3                                                                              H                                         1143   3-cyclo-C.sub.6 H.sub.11                                                                          OCH.sub.3                                                                              H                                         1144   4-cyclo-C.sub.6 H.sub.11                                                                          OCH.sub.3                                                                              H                                         1145   2-Cl, 4-C.sub.6 H.sub.5                                                                           OCH.sub.3                                                                              H                                         1146   2-Br, 4-C.sub.6 H.sub.5                                                                           OCH.sub.3                                                                              H                                         1147   2-OCH.sub.3         OCH.sub.3                                                                              H                                         1148   3-OCH.sub.3         OCH.sub.3                                                                              H                                         1149   4-OCH.sub.3         OCH.sub.3                                                                              H                                         1150   2-OC.sub.2 H.sub.5  OCH.sub.3                                                                              H                                         1151   3-O--C.sub.2 H.sub.5                                                                              OCH.sub.3                                                                              H                                         1152   4-O--C.sub.2 H.sub.5                                                                              OCH.sub.3                                                                              H                                         1153   2-O-n-C.sub.3 H.sub.7                                                                             OCH.sub.3                                                                              H                                         1154   3-O-n-C.sub.3 H.sub.7                                                                             OCH.sub.3                                                                              H                                         1155   4-O-n-C.sub.3 H.sub.7                                                                             OCH.sub.3                                                                              H                                         1156   2-O-i-C.sub.3 H.sub.7                                                                             OCH.sub.3                                                                              H                                         1157   3-O-i-C.sub.3 H.sub.7                                                                             OCH.sub.3                                                                              H                                         1158   4-O-i-C.sub.3 H.sub.7                                                                             OCH.sub.3                                                                              H                                         1159   2-O-n-C.sub.6 H.sub.13                                                                            OCH.sub.3                                                                              H                                         1160   3-O-n-C.sub.6 H.sub.13                                                                            OCH.sub.3                                                                              H                                         1161   4-O-n-C.sub.6 H.sub.13                                                                            OCH.sub.3                                                                              H                                         1162   2-O--CH.sub.2 C.sub.6 H.sub.5                                                                     OCH.sub.3                                                                              H                                         1163   3-O--CH.sub.2 C.sub.6 H.sub.5                                                                     OCH.sub.3                                                                              H                                         1164   4-O--CH.sub.2 C.sub.6 H.sub.5                                                                     OCH.sub.3                                                                              H                                         1165   2-O--(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                             OCH.sub.3                                                                              H                                         1166   4-O--(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                             OCH.sub.3                                                                              H                                         1167   2,3-(OCH.sub.3).sub.2                                                                             OCH.sub.3                                                                              H                                         1168   2,4-(OCH.sub.3).sub.2                                                                             OCH.sub.3                                                                              H                                         1169   2,5-(OCH.sub.3).sub.2                                                                             OCH.sub.3                                                                              H                                         1170   2,6-(OCH.sub.3).sub.2                                                                             OCH.sub.3                                                                              H                                         1171   3,4-(OCH.sub.3).sub.2                                                                             OCH.sub.3                                                                              H                                         1172   3,5-(OCH.sub.3).sub.2                                                                             OCH.sub.3                                                                              H                                         1173   2-O-t-C.sub.4 H.sub.9                                                                             OCH.sub.3                                                                              H                                         1174   3-O-t-C.sub.4 H.sub.9                                                                             OCH.sub.3                                                                              H                                         1175   4-O-t-C.sub.4 H.sub.9                                                                             OCH.sub.3                                                                              H                                         1176   3-(3'-Cl--C.sub.6 H.sub.4)                                                                        OCH.sub.3                                                                              H                                         1177   4-(4'-CH.sub.3 --C.sub.6 H.sub.4)                                                                 OCH.sub.3                                                                              H                                         1178   2-O--C.sub.6 H.sub.5                                                                              OCH.sub.3                                                                              H                                         1179   3-O--C.sub.6 H.sub.5                                                                              OCH.sub.3                                                                              H                                         1180   4-O--C.sub.6 H.sub.5                                                                              OCH.sub.3                                                                              H                                         1181   2-O-(2'-F--C.sub.6 H.sub.4)                                                                       OCH.sub.3                                                                              H                                         1182   3-O-(3'-Cl--C.sub.6 H.sub.4)                                                                      OCH.sub.3                                                                              H                                         1183   4-O-(4'-CH.sub.3 --C.sub.6 H.sub.4)                                                               OCH.sub.3                                                                              H                                         1184   2,3,6-(CH.sub.3).sub.3, 4-F                                                                       OCH.sub.3                                                                              H                                         1185   2,3,6-(CH.sub.3).sub.3, 4-Cl                                                                      OCH.sub.3                                                                              H                                         1186   2,3,6-(CH.sub.3).sub.3, 4-Br                                                                      OCH.sub.3                                                                              H                                         1187   2,4-(CH.sub.3).sub.2, 6-F                                                                         OCH.sub.3                                                                              H                                         1188   2,4-(CH.sub.3).sub.2, 6-Cl                                                                        OCH.sub.3                                                                              H                                         1189   2,4-(CH.sub.3).sub.2, 6-Br                                                                        OCH.sub.3                                                                              H                                         1190   2-i-CH.sub.3 H.sub.1, 4-Cl, 5-CH.sub.3                                                            OCH.sub.3                                                                              H                                         1191   2-Cl, 4-NO.sub.2    OCH.sub.3                                                                              H                                         1192   2-NO.sub.2, 4-Cl    OCH.sub.3                                                                              H                                         1193   2-OCH.sub.3, 5-NO.sub.2                                                                           OCH.sub.3                                                                              H                                         1194   2,4-Cl.sub.2, 5-NO.sub.2                                                                          OCH.sub.3                                                                              H                                         1195   2,4-Cl.sub.2, 6-NO.sub.2                                                                          OCH.sub.3                                                                              H                                         1196   2,6-Cl.sub.2, 4-NO.sub.2                                                                          OCH.sub.3                                                                              H                                         1197   2,6-Br.sub.2, 4-NO.sub.2                                                                          OCH.sub.3                                                                              H                                         1198   2,6-I.sub.2, 4-NO.sub.2                                                                           OCH.sub.3                                                                              H                                         1199   2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl                                                             OCH.sub.3                                                                              H                                         1200   2-CO.sub.2 CH.sub.3 OCH.sub.3                                                                              H                                         1201   3-CO.sub.2 CH.sub.3 OCH.sub.3                                                                              H                                         1202   4-CO.sub.2 CH.sub.3 OCH.sub.3                                                                              H                                         1203   2-CH.sub.2 --OCH.sub.3                                                                            OCH.sub.3                                                                              H                                         1204   3-CH.sub.2 --OCH.sub.3                                                                            OCH.sub.3                                                                              H                                         1205   4-CH.sub.2 --OCH.sub.3                                                                            OCH.sub.3                                                                              H                                         1206   2-Me-4-CH.sub.3 --CH(CH.sub.3)--CO                                                                OCH.sub.3                                                                              H                                         1207   2-CH.sub.3 -4-(CH.sub.3 --C═NOCH.sub.3)                                                       OCH.sub.3                                                                              H                                         1208   2-CH.sub.3 -4-(CH.sub.3 --C═NOC.sub.2 H.sub.5)                                                OCH.sub.3                                                                              H                                         1209   2-CH.sub.3 -4-(CH.sub.3 --C═NO-n-C.sub.3 H.sub.7)                                             OCH.sub.3                                                                              H                                         1210   2-CH.sub.3 -4-(CH.sub.3 --C═NO-i-C.sub.3 H.sub.7)                                             OCH.sub.3                                                                              H                                         1211   2,5-(CH.sub.3)2-4-(CH.sub.3 --C═NOCH.sub.3)                                                   OCH.sub.3                                                                              H                                         1212   2,5-(CH.sub.3)2-4-(CH.sub.3 --C═NOC.sub.2 H.sub.5)                                            OCH.sub.3                                                                              H                                         1213   2,5-(CH.sub.3 -4-(CH.sub.3 --C═NO-n-C.sub.3 H.sub.7)                                          OCH.sub.3                                                                              H                                         1214   2,5-(CH.sub.3).sub.2 -4-(CH.sub.3 --C═NO-i-C.sub.3 H.sub.7)                                   OCH.sub.3                                                                              H                                         1215   2-C.sub.6 H.sub.5   OCH.sub.3                                                                              H                                         1216   3-C.sub.6 H.sub.5   OCH.sub.3                                                                              H                                         1217   4-C.sub.6 H.sub.5   OCH.sub.3                                                                              H                                         1218   2-(2'-F--C.sub.6 H.sub.4)                                                                         OCH.sub.3                                                                              H                                         1219   2-CH.sub.3, 5-Br    OCH.sub.3                                                                              H                                         1220   2-CH.sub.3, 6-Br    OCH.sub.3                                                                              H                                         1221   2-Cl, 3-CH.sub.3    OCH.sub.3                                                                              H                                         1222   2-Cl, 4-CH.sub.3    OCH.sub.3                                                                              H                                         1223   2-Cl, 5-CH.sub.3    OCH.sub.3                                                                              H                                         1224   2-F, 3-CH.sub.3     OCH.sub.3                                                                              H                                         1225   2-F, 4-CH.sub.3     OCH.sub.3                                                                              H                                         1226   2-F, 5-CH.sub.3     OCH.sub.3                                                                              H                                         1227   2-Br, 3-CH.sub.3    OCH.sub.3                                                                              H                                         1228   2-Br, 4-CH.sub.3    OCH.sub.3                                                                              H                                         1229   2-Br, 5-CH.sub.3    OCH.sub.3                                                                              H                                         1230   3-CH.sub.3, 4-Cl    OCH.sub.3                                                                              H                                         1231   3-CH.sub.3, 5-Cl    OCH.sub.3                                                                              H                                         1232   3-CH.sub.3, 4-F     OCH.sub.3                                                                              H                                         1233   3-CH.sub.3, 5-F     OCH.sub.3                                                                              H                                         1234   3-CH.sub.3, 4-Br    OCH.sub.3                                                                              H                                         1235   3-CH.sub.3, 5-Br    OCH.sub.3                                                                              H                                         1236   3-F, 4-CH.sub.3     OCH.sub.3                                                                              H                                         1237   3-Cl, 4-CH.sub.3    OCH.sub.3                                                                              H                                         1238   3-Br, 4-CH.sub.3    OCH.sub.3                                                                              H                                         1239   2-Cl, 4,5-(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                              H                                         1240   2-Br, 4,5-(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                              H                                         1241   2-Cl, 3,5-(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                              H                                         1242   2-Br, 3,5-(CH.sub.3).sub.2                                                                        OCH.sub.3                                                                              H                                         1243   2,6-Cl.sub.2, 4-CH.sub.3                                                                          OCH.sub.3                                                                              H                                         1244   2,6-F.sub.2, 4-CH.sub.3                                                                           OCH.sub.3                                                                              H                                         1245   2,6-Br.sub.2, 4-CH.sub.3                                                                          OCH.sub.3                                                                              H                                         1246   2,4-Br.sub.2, 6-CH.sub.3                                                                          OCH.sub.3                                                                              H                                         1247   2,4-F.sub.2, 6-CH.sub.3                                                                           OCH.sub.3                                                                              H                                         1248   2,4-Br.sub.2, 6-CH.sub.3                                                                          OCH.sub.3                                                                              H                                         1249   2,6-(CH.sub.3).sub.2, 4-F                                                                         OCH.sub.3                                                                              H                                         1250   2,6-(CH.sub.3).sub.2, 4-Cl                                                                        OCH.sub.3                                                                              H                                         1251   2,6-(CH.sub.3).sub.2, 4-Br                                                                        OCH.sub.3                                                                              H                                         1252   3,5-(CH.sub.3).sub.2, 4-F                                                                         OCH.sub.3                                                                              H                                         1253   3,5-(CH.sub.3).sub.2, 4-Cl                                                                        OCH.sub.3                                                                              H                                         1254   3,5-(CH.sub.3).sub.2, 4-Br                                                                        OCH.sub.3                                                                              H                                         1255   2-CF.sub.3          OCH.sub.3                                                                              H                                         1256   3-CF.sub.3          OCH.sub.3                                                                              H                                         1257   4-CF.sub.3          OCH.sub.3                                                                              H                                         1258   2-OCF.sub.3         OCH.sub.3                                                                              H                                         1259   3-OCF.sub.3         OCH.sub.3                                                                              H                                         1260   4-OCF.sub.3         OCH.sub.3                                                                              H                                         1261   3-OCH.sub.2 CHF.sub.2                                                                             OCH.sub.3                                                                              H                                         1262   2-NO.sub.2          OCH.sub.3                                                                              H                                         1263   3-NO.sub.2          OCH.sub.3                                                                              H                                         1264   4-NO.sub.2          OCH.sub.3                                                                              H                                         1265   2-CN                OCH.sub.3                                                                              H                                         1266   3-CN                OCH.sub.3                                                                              H                                         1267   4-CN                OCH.sub.3                                                                              H                                         1268   2-CH.sub.3, 3-Cl    OCH.sub.3                                                                              H                                         1269   2-CH.sub.3, 4-Cl    OCH.sub.3                                                                              H                                         1270   2-CH.sub.3, 5-Cl    OCH.sub.3                                                                              H                                         1271   2-CH.sub.3, 6-Cl    OCH.sub.3                                                                              H                                         1272   2-CH.sub.3, 3-F     OCH.sub.3                                                                              H                                         1273   2-CH.sub.3, 4-F     OCH.sub.3                                                                              H                                         1274   2-CH.sub.3, 5-F     OCH.sub.3                                                                              H                                         1275   2-CH.sub.3, 6-F     OCH.sub.3                                                                              H                                         1276   2-CH.sub.3, 3-Br    OCH.sub.3                                                                              H                                         1277   2-CH.sub.3, 4-Br    OCH.sub.3                                                                              H                                         1278   2-Pyridyl-2'        OCH.sub.3                                                                              H                                         1279   3-Pyridyl-3'        OCH.sub.3                                                                              H                                         1280   4-Pyridyl-4'        OCH.sub.3                                                                              H                                         1281   2-CO--CH.sub.3      OCH.sub.3                                                                              H                                         1282   3-CO--CH.sub.3      OCH.sub.3                                                                              H                                         1283   4-CO--CH.sub.3      OCH.sub.3                                                                              H                                         1284   2-C(═N--OCH.sub.3)--CH.sub.3                                                                  OCH.sub.3                                                                              H                                         1285   3-C(═N--OCH.sub.3)--CH.sub.3                                                                  OCH.sub.3                                                                              H                                         1286   4-C(═N--OCH.sub.3)--CH.sub.3                                                                  OCH.sub.3                                                                              H                                         1287   2-F                 CH.sub.3 5-CH.sub.3                                1288   3-F                 CH.sub.3 5-CH.sub.3                                1289   4-F                 CH.sub.3 5-CH.sub.3                                1290   2,4-F.sub.2         CH.sub.3 5-CH.sub.3                                1291   2,4,6-F.sub.3       CH.sub.3 5-CH.sub.3                                1292   2,3,4,5,6-F.sub.5   CH.sub.3 5-CH.sub.3                                1293   2,3-F.sub.2         CH.sub.3 5-CH.sub.3                                1294   2-Cl                CH.sub.3 5-CH.sub.3                                1295   3-Cl                CH.sub.3 5-CH.sub.3                                1296   4-Cl                CH.sub.3 5-CH.sub.3                                1297   2,3-Cl.sub.2        CH.sub.3 5-CH.sub.3                                1298   2,4-Cl.sub.2        CH.sub.3 5-CH.sub.3                                1299   2,5-Cl.sub.2        CH.sub.3 5-CH.sub.3                                1300   2,6-Cl.sub.2        CH.sub.3 5-CH.sub.3                                1301   3,4-Cl.sub.2        CH.sub.3 5-CH.sub.3                                1302   3,5-Cl.sub.2        CH.sub.3 5-CH.sub.3                                1303   2,3,4-Cl.sub.3      CH.sub.3 5-CH.sub.3                                1304   2,3,5-Cl.sub.3      CH.sub.3 5-CH.sub.3                                1305   2,3,6-Cl.sub.3      CH.sub.3 5-CH.sub.3                                1306   2,4,5-Cl.sub.3      CH.sub.3 5-CH.sub.3                                1307   2,4,6-Cl.sub.3      CH.sub.3 5-CH.sub.3                                1308   3,4,5-Cl.sub.3      CH.sub.3 5-CH.sub.3                                1309   2,3,4,6-Cl.sub.4    CH.sub.3 5-CH.sub.3                                1310   2,3,5,6-Cl.sub.4    CH.sub.3 5-CH.sub.3                                1311   2,3,4,5,6-Cl.sub.5  CH.sub.3 5-CH.sub.3                                1312   2-Br                CH.sub.3 5-CH.sub.3                                1313   3-Br                CH.sub.3 5-CH.sub.3                                1314   4-Br                CH.sub.3 5-CH.sub.3                                1315   2,4-Br.sub.2        CH.sub.3 5-CH.sub.3                                1316   2,5-Br.sub.2        CH.sub.3 5-CH.sub.3                                1317   2,6-Br.sub.2        CH.sub.3 5-CH.sub.3                                1318   2,4,6-Br.sub.3      CH.sub.3 5-CH.sub.3                                1319   2,3,4,5,6-Br.sub.5  CH.sub.3 5-CH.sub.3                                1320   2-I                 CH.sub.3 5-CH.sub.3                                1321   3-I                 CH.sub.3 5-CH.sub.3                                1322   4-I                 CH.sub.3 5-CH.sub.3                                1323   2,4-I.sub.2         CH.sub.3 5-CH.sub.3                                1324   2-Cl, 3-F           CH.sub.3 5-CH.sub.3                                1325   2-Cl, 4-F           CH.sub.3 5-CH.sub.3                                1326   2-Cl, 5-F           CH.sub.3 5-CH.sub.3                                1327   2-Cl, 6-F           CH.sub.3 5-CH.sub.3                                1328   2-Cl, 3-Br          CH.sub.3 5-CH.sub.3                                1329   2-Cl, 4-Br          CH.sub.3 5-CH.sub.3                                1330   2-Cl, 5-Br          CH.sub.3 5-CH.sub.3                                1331   2-Cl, 6-Br          CH.sub.3 5-CH.sub.3                                1332   2-Br, 3-Cl          CH.sub.3 5-CH.sub.3                                1333   2-Br, 4-Cl          CH.sub.3 5-CH.sub.3                                1334   2-Br, 5-Cl          CH.sub.3 5-CH.sub.3                                1335   2-Br, 3-F           CH.sub.3 5-CH.sub.3                                1336   2-Br, 4-F           CH.sub.3 5-CH.sub.3                                1337   2-Br, 5-F           CH.sub.3 5-CH.sub.3                                1338   2-Br, 6-F           CH.sub.3 5-CH.sub.3                                1339   2-F, 3-Cl           CH.sub.3 5-CH.sub.3                                1340   2-F, 4-Cl           CH.sub.3 5-CH.sub.3                                1341   2-F, 5-Cl           CH.sub.3 5-CH.sub.3                                1342   3-Cl, 4-F           CH.sub.3 5-CH.sub.3                                1343   3-Cl, 5-F           CH.sub.3 5-CH.sub.3                                1344   3-Cl, 4-Br          CH.sub.3 5-CH.sub.3                                1345   3-Cl, 5-Br          CH.sub.3 5-CH.sub.3                                1346   3-F, 4-Cl           CH.sub.3 5-CH.sub.3                                1347   3-F, 4-Br           CH.sub.3 5-CH.sub.3                                1348   3-Br, 4-Cl          CH.sub.3 5-CH.sub.3                                1349   3-Br, 4-F           CH.sub.3 5-CH.sub.3                                1350   2,6-Cl.sub.2, 4-Br  CH.sub.3 5-CH.sub.3                                1351   2-CH.sub.3          CH.sub.3 5-CH.sub.3                                1352   3-CH.sub.3          CH.sub.3 5-CH.sub.3                                1353   4-CH.sub.3          CH.sub.3 5-CH.sub.3                                1354   2,3-(CH.sub.3).sub.2                                                                              CH.sub.3 5-CH.sub.3                                1355   2,4-(CH.sub.3).sub.2                                                                              CH.sub.3 5-CH.sub.3                                1356   2,5-(CH.sub.3).sub.2                                                                              CH.sub.3 5-CH.sub.3                                1357   2,6-(CH.sub.3).sub.2                                                                              CH.sub.3 5-CH.sub.3                                1358   3,4-(CH.sub.3).sub.2                                                                              CH.sub.3 5-CH.sub.3                                1359   3,5-(CH.sub.3).sub.2                                                                              CH.sub.3 5-CH.sub.3                                1360   2,3,5-(CH.sub.3).sub.3                                                                            CH.sub.3 5-CH.sub.3                                1361   2,3,4-(CH.sub.3).sub.3                                                                            CH.sub.3 5-CH.sub.3                                1362   2,3,6-(CH.sub.3).sub.3                                                                            CH.sub.3 5-CH.sub.3                                1363   2,4,5-(CH.sub.3).sub.3                                                                            CH.sub.3 5-CH.sub.3                                1364   2,4,6-(CH.sub.3).sub.3                                                                            CH.sub.3 5-CH.sub.3                                1365   3,4,5-(CH.sub.3).sub.3                                                                            CH.sub.3 5-CH.sub.3                                1366   2,3,4,6-(CH.sub.3).sub.4                                                                          CH.sub.3 5-CH.sub.3                                1367   2,3,5,6-(CH.sub.3).sub.4                                                                          CH.sub.3 5-CH.sub.3                                1368   2,3,4,5,6-(CH.sub.3).sub.5                                                                        CH.sub.3 5-CH.sub.3                                1369   2-C.sub.2 H.sub.5   CH.sub.3 5-CH.sub.3                                1370   3-C.sub.2 H.sub.5   CH.sub.3 5-CH.sub.3                                1371   4-C.sub.2 H.sub.5   CH.sub.3 5-CH.sub.3                                1372   2,4-(C.sub.2 H.sub.5).sub.5                                                                       CH.sub.3 5-CH.sub.3                                1373   2,6-(C.sub.2 H.sub.5).sub.2                                                                       CH.sub.3 5-CH.sub.3                                1374   3,5-(C.sub.2 H.sub.5).sub.2                                                                       CH.sub.3 5-CH.sub.3                                1375   2,4,6-(C.sub.2 H.sub.5).sub.3                                                                     CH.sub.3 5-CH.sub.3                                1376   2-n-C.sub.3 H.sub.7 CH.sub.3 5-CH.sub.3                                1377   3-n-C.sub.3 H.sub.7 CH.sub.3 5-CH.sub.3                                1378   4-n-C.sub.3 H.sub.7 CH.sub.3 5-CH.sub.3                                1379   2-i-C.sub.3 H.sub.7 CH.sub.3 5-CH.sub.3                                1380   3-i-C.sub.3 H.sub.7 CH.sub.3 5-CH.sub.3                                1381   4-i-C.sub.3 H.sub.7 CH.sub.3 5-CH.sub.3                                1382   2,4-(i-C.sub.3 H.sub.7).sub.2                                                                     CH.sub.3 5-CH.sub.3                                1383   2,6-(i-C.sub.3 H.sub.7).sub.2                                                                     CH.sub.3 5-CH.sub.3                                1384   3,5-(i-C.sub.3 H.sub.7).sub.2                                                                     CH.sub.3 5-CH.sub.3                                1385   2-s-C.sub.4 H.sub.9 CH.sub.3 5-CH.sub.3                                1386   3-s-C.sub.4 H.sub.9 CH.sub.3 5-CH.sub.3                                1387   4-s-C.sub.4 H.sub.9 CH.sub.3 5-CH.sub.3                                1388   2-t-C.sub.4 H.sub.9 CH.sub.3 5-CH.sub.3                                1389   3-t-C.sub.4 H.sub.9 CH.sub.3 5-CH.sub.3                                1390   4-t-C.sub.4 H.sub.9 CH.sub.3 5-CH.sub.3                                1391   4-n-C.sub.9 H.sub.19                                                                              CH.sub.3 5-CH.sub.3                                1392   2-CH.sub.3, 4-t-C.sub.4 H.sub.9                                                                   CH.sub.3 5-CH.sub.3                                1393   2-CH.sub.3, 6-t-C.sub.4 H.sub.9                                                                   CH.sub.3 5-CH.sub.3                                1394   2-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                   CH.sub.3 5-CH.sub.3                                1395   2-CH.sub.3, 5-i-C.sub.3 H.sub.7                                                                   CH.sub.3 5-CH.sub.3                                1396   3-CH.sub.3, 4-i-C.sub.3 H.sub.7                                                                   CH.sub.3 5-CH.sub.3                                1397   2-cyclo-C.sub.6 H.sub.11                                                                          CH.sub.3 5-CH.sub.3                                1398   3-cyclo-C.sub.6 H.sub.11                                                                          CH.sub.3 5-CH.sub.3                                1399   4-cyclo-C.sub.6 H.sub.11                                                                          CH.sub.3 5-CH.sub.3                                1400   2-Cl, 4-C.sub.6 H.sub.5                                                                           CH.sub.3 5-CH.sub.3                                1401   2-Br, 4-C.sub.6 H.sub.5                                                                           CH.sub.3 5-CH.sub.3                                1402   2-OCH.sub.3         CH.sub.3 5-CH.sub.3                                1403   3-OCH.sub.3         CH.sub.3 5-CH.sub.3                                1404   4-OCH.sub.3         CH.sub.3 5-CH.sub.3                                1405   2-OC.sub.2 H.sub.5  CH.sub.3 5-CH.sub.3                                1406   3-O--C.sub.2 H.sub.5                                                                              CH.sub.3 5-CH.sub.3                                1407   4-O--C.sub.2 H.sub.5                                                                              CH.sub.3 5-CH.sub.3                                1408   2-O-n-C.sub.3 H.sub.7                                                                             CH.sub.3 5-CH.sub.3                                1409   3-O-n-C.sub.3 H.sub.7                                                                             CH.sub.3 5-CH.sub.3                                1410   4-O-n-C.sub.3 H.sub.7                                                                             CH.sub.3 5-CH.sub.3                                1411   2-O-i-C.sub.3 H.sub.7                                                                             CH.sub.3 5-CH.sub.3                                1412   3-O-i-C.sub.3 H.sub.7                                                                             CH.sub.3 5-CH.sub.3                                1413   4-O-i-C.sub.3 H.sub.7                                                                             CH.sub.3 5-CH.sub.3                                1414   2-O-n-C.sub.6 H.sub.13                                                                            CH.sub.3 5-CH.sub.3                                1415   3-O-n-C.sub.6 H.sub.13                                                                            CH.sub.3 5-CH.sub.3                                1416   4-O-n-C.sub.6 H.sub.13                                                                            CH.sub.3 5-CH.sub.3                                1417   2-O--CH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.3 5-CH.sub.3                                1418   3-O--CH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.3 5-CH.sub.3                                1419   4-O--CH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.3 5-CH.sub.3                                1420   2-O--(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                             CH.sub.3 5-CH.sub.3                                1421   4-O--(CH.sub.2).sub.3 C.sub.6 H.sub.5                                                             CH.sub.3 5-CH.sub.3                                1422   2,3-(OCH.sub.3).sub.2                                                                             CH.sub.3 5-CH.sub.3                                1423   2,4-(OCH.sub.3).sub.2                                                                             CH.sub.3 5-CH.sub.3                                1424   2,5-(OCH.sub.3).sub.2                                                                             CH.sub.3 5-CH.sub.3                                1425   2,6-(OCH.sub.3).sub.2                                                                             CH.sub.3 5-CH.sub.3                                1426   3,4-(OCH.sub.3).sub.2                                                                             CH.sub.3 5-CH.sub.3                                1427   3,5-(OCH.sub.3).sub.2                                                                             CH.sub.3 5-CH.sub.3                                1428   2-O-t-C.sub.4 H.sub.9                                                                             CH.sub.3 5-CH.sub.3                                1429   3-O-t-C.sub.4 H.sub.9                                                                             CH.sub.3 5-CH.sub.3                                1430   4-O-t-C.sub.4 H.sub.9                                                                             CH.sub.3 5-CH.sub.3                                1431   3-(3'-Cl--C.sub.6 H.sub.4)                                                                        CH.sub.3 5-CH.sub.3                                1432   4-(4'-CH.sub.3 --C.sub.6 H.sub.4)                                                                 CH.sub.3 5-CH.sub.3                                1433   2-O--C.sub.6 H.sub.5                                                                              CH.sub.3 5-CH.sub.3                                1434   3-O--C.sub.6 H.sub.5                                                                              CH.sub.3 5-CH.sub.3                                1435   4-O--C.sub.6 H.sub.5                                                                              CH.sub.3 5-CH.sub.3                                1436   2-O-(2'-F--C.sub.6 H.sub.4)                                                                       CH.sub.3 5-CH.sub.3                                1437   3-O-(3'-Cl--C.sub.6 H.sub.4)                                                                      CH.sub.3 5-CH.sub.3                                1438   4-O-(4'-CH.sub.3 --C.sub.6 H.sub.4)                                                               CH.sub.3 5-CH.sub.3                                1439   2,3,6-(CH.sub.3).sub.3, 4-F                                                                       CH.sub.3 5-CH.sub.3                                1440   2,3,6-(CH.sub.3).sub.3, 4-Cl                                                                      CH.sub.3 5-CH.sub.3                                1441   2,3,6-(CH.sub.3).sub.3, 4-Br                                                                      CH.sub.3 5-CH.sub.3                                1442   2,4-(CH.sub.3).sub.2, 6-F                                                                         CH.sub.3 5-CH.sub.3                                1443   2,4-(CH.sub.3).sub.2, 6-Cl                                                                        CH.sub.3 5-CH.sub.3                                1444   2,4-(CH.sub.3).sub.2, 6-Br                                                                        CH.sub.3 5-CH.sub.3                                1445   2-i-CH.sub.3 H.sub.1, 4-Cl, 5-CH.sub.3                                                            CH.sub.3 5-CH.sub.3                                1446   2-Cl, 4-NO.sub.2    CH.sub.3 5-CH.sub.3                                1447   2-NO.sub.2, 4-Cl    CH.sub.3 5-CH.sub.3                                1448   2-OCH.sub.3, 5-NO.sub.2                                                                           CH.sub.3 5-CH.sub.3                                1449   2,4-Cl.sub.2, 5-NO.sub.2                                                                          CH.sub.3 5-CH.sub.3                                1450   2,4-Cl.sub.2, 6-NO.sub.2                                                                          CH.sub.3 5-CH.sub.3                                1451   2,6-Cl.sub.2, 4-NO.sub.2                                                                          CH.sub.3 5-CH.sub.3                                1452   2,6-Br.sub.2, 4-NO.sub.2                                                                          CH.sub.3 5-CH.sub.3                                1453   2,6-I.sub.2, 4-NO.sub.2                                                                           CH.sub.3 5-CH.sub.3                                1454   2-CH.sub.3, 5-i-CH.sub.3 H.sub.7, 4-Cl                                                            CH.sub.3 5-CH.sub.3                                1455   2-CO.sub.2 CH.sub.3 CH.sub.3 5-CH.sub.3                                1456   3-CO.sub.2 CH.sub.3 CH.sub.3 5-CH.sub.3                                1457   4-CO.sub.2 CH.sub.3 CH.sub.3 5-CH.sub.3                                1458   2-CH.sub.2 --OCH.sub.3                                                                            CH.sub.3 5-CH.sub.3                                1459   3-CH.sub.2 --OCH.sub.3                                                                            CH.sub.3 5-CH.sub.3                                1460   4-CH.sub.2 --OCH.sub.3                                                                            CH.sub.3 5-CH.sub.3                                1461   2-Me-4-CH.sub.3 --CH(CH.sub.3)--CO                                                                CH.sub.3 5-CH.sub.3                                1462   2-CH.sub.3 -4-(CH.sub.3 --C═NOCH.sub.3)                                                       CH.sub.3 5-CH.sub.3                                1463   2-CH.sub.3 -4-(CH.sub.3 --C═NOC.sub.2 H.sub.5)                                                CH.sub.3 5-CH.sub.3                                1464   2-CH.sub.3 -4-(CH.sub.3 --C═NO-n-C.sub.3 H.sub.7)                                             CH.sub.3 5-CH.sub.3                                1465   2-CH.sub.3 -4-(CH.sub.3 --C═NO-i-C.sub.3 H.sub.7)                                             CH.sub.3 5-CH.sub.3                                1466   2,5-(CH.sub.3).sub.2 -4-(CH.sub.3 --C═NOCH.sub.3)                                             CH.sub.3 5-CH.sub.3                                1467   2,5-(CH.sub.3).sub.2 -4-(CH.sub.3 --C═NOC.sub.2 H.sub.5)                                      CH.sub.3 5-CH.sub.3                                1468   2,5-(CH.sub.3 -4-(CH.sub.3 --C═NO-n-C.sub.3 H.sub.7)                                          CH.sub.3 5-CH.sub.3                                1469   2,5-(CH.sub.3).sub.2 -4-(CH.sub.3 --C═NO-i-C.sub.3 H.sub.7)                                   CN       5-CH.sub.3                                1470   2-C.sub.6 H.sub.5   CH.sub.3 5-CH.sub.3                                1471   3-C.sub.6 H.sub.5   CH.sub.3 5-CH.sub.3                                1472   4-C.sub.6 H.sub.5   CH.sub.3 5-CH.sub.3                                1473   2-(2'-F--C.sub.6 H.sub.4)                                                                         CH.sub.3 5-CH.sub.3                                1474   2-CH.sub.3, 5-Br    CH.sub.3 5-CH.sub.3                                1475   2-CH.sub.3, 6-Br    CH.sub.3 5-CH.sub.3                                1476   2-Cl, 3-CH.sub.3    CH.sub.3 5-CH.sub.3                                1477   2-Cl, 4-CH.sub.3    CH.sub.3 5-CH.sub.3                                1478   2-Cl, 5-CH.sub.3    CH.sub.3 5-CH.sub.3                                1479   2-F, 3-CH.sub.3     CH.sub.3 5-CH.sub.3                                1480   2-F, 4-CH.sub.3     CH.sub.3 5-CH.sub.3                                1481   2-F, 5-CH.sub.3     CH.sub.3 5-CH.sub.3                                1482   2-Br, 3-CH.sub.3    CH.sub.3 5-CH.sub.3                                1483   2-Br, 4-CH.sub.3    CH.sub.3 5-CH.sub.3                                1484   2-Br, 5-CH.sub.3    CH.sub.3 5-CH.sub.3                                1485   3-CH.sub.3, 4-Cl    CH.sub.3 5-CH.sub.3                                1486   3-CH.sub.3, 5-Cl    CH.sub.3 5-CH.sub.3                                1487   3-CH.sub.3, 4-F     CH.sub.3 5-CH.sub.3                                1488   3-CH.sub.3, 5-F     CH.sub.3 5-CH.sub.3                                1489   3-CH.sub.3, 4-Br    CH.sub.3 5-CH.sub.3                                1490   3-CH.sub.3, 5-Br    CH.sub.3 5-CH.sub.3                                1491   3-F, 4-CH.sub.3     CH.sub.3 5-CH.sub.3                                1492   3-Cl, 4-CH.sub.3    CH.sub.3 5-CH.sub.3                                1493   3-Br, 4-CH.sub.3    CH.sub.3 5-CH.sub.3                                1494   2-Cl, 4,5-(CH.sub.3).sub.2                                                                        CH.sub.3 5-CH.sub.3                                1495   2-Br, 4,5-(CH.sub.3).sub.2                                                                        CH.sub.3 5-CH.sub.3                                1496   2-Cl, 3,5-(CH.sub.3).sub.2                                                                        CH.sub.3 5-CH.sub.3                                1497   2-Br, 3,5-(CH.sub.3).sub.2                                                                        CH.sub.3 5-CH.sub.3                                1498   2,6-Cl.sub.2, 4-CH.sub.3                                                                          CH.sub.3 5-CH.sub.3                                1499   2,6-F.sub.2, 4-CH.sub.3                                                                           CH.sub.3 5-CH.sub.3                                1500   2,6-Br.sub.2, 4-CH.sub.3                                                                          CH.sub.3 5-CH.sub.3                                1501   2,4-Br.sub.2, 6-CH.sub.3                                                                          CH.sub.3 5-CH.sub.3                                1502   2,4-F.sub.2, 6-CH.sub.3                                                                           CH.sub.3 5-CH.sub.3                                1503   2,4-Br.sub.2, 6-CH.sub.3                                                                          CH.sub.3 5-CH.sub.3                                1504   2,6-(CH.sub.3).sub.2, 4-F                                                                         CH.sub.3 5-CH.sub.3                                1505   2,6-(CH.sub.3).sub.2, 4-Cl                                                                        CH.sub.3 5-CH.sub.3                                1506   2,6-(CH.sub.3).sub.2, 4-Br                                                                        CH.sub.3 5-CH.sub.3                                1507   3,5-(CH.sub.3).sub.2, 4-F                                                                         CH.sub.3 5-CH.sub.3                                1508   3,5-(CH.sub.3).sub.2, 4-Cl                                                                        CH.sub.3 5-CH.sub.3                                1509   3,5-(CH.sub.3).sub.2, 4-Br                                                                        CH.sub.3 5-CH.sub.3                                1510   2-CF.sub.3          CH.sub.3 5-CH.sub.3                                1511   3-CF.sub.3          CH.sub.3 5-CH.sub.3                                1512   4-CF.sub.3          CH.sub.3 5-CH.sub.3                                1513   2-OCF.sub.3         CH.sub.3 5-CH.sub.3                                1514   3-OCF.sub.3         CH.sub.3 5-CH.sub.3                                1515   4-OCF.sub.3         CH.sub.3 5-CH.sub.3                                1516   3-OCH.sub.2 CHF.sub.2                                                                             CH.sub.3 5-CH.sub.3                                1517   2-NO.sub.2          CH.sub.3 5-CH.sub.3                                1518   3-NO.sub.2          CH.sub.3 5-CH.sub.3                                1519   4-NO.sub.2          CH.sub.3 5-CH.sub.3                                1520   2-CN                CH.sub.3 5-CH.sub.3                                1521   3-CN                CH.sub.3 5-CH.sub.3                                1522   4-CN                CH.sub.3 5-CH.sub.3                                1523   2-CH.sub.3, 3-Cl    CH.sub.3 5-CH.sub.3                                1524   2-CH.sub.3, 4-Cl    CH.sub.3 5-CH.sub.3                                1525   2-CH.sub.3, 5-Cl    CH.sub.3 5-CH.sub.3                                1526   2-CH.sub.3, 6-Cl    CH.sub.3 5-CH.sub.3                                1527   2-CH.sub.3, 3-F     CH.sub.3 5-CH.sub.3                                1528   2-CH.sub.3, 4-F     CH.sub.3 5-CH.sub.3                                1529   2-CH.sub.3, 5-F     CH.sub.3 5-CH.sub.3                                1530   2-CH.sub.3, 6-F     CH.sub.3 5-CH.sub.3                                1531   2-CH.sub.3, 3-Br    CH.sub.3 5-CH.sub.3                                1532   2-CH.sub.3, 4-Br    CH.sub.3 5-CH.sub.3                                1533   2-Pyridyl-2'        CH.sub.3 5-CH.sub.3                                1534   3-Pyridyl-3'        CH.sub.3 5-CH.sub.3                                1535   4-Pyridyl-4'        CH.sub.3 5-CH.sub.3                                1536   2-CO--CH.sub.3      CH.sub.3 5-CH.sub.3                                1537   3-CO--CH.sub.3      CH.sub.3 5-CH.sub.3                                1538   4-CO--CH.sub.3      CH.sub.3 5-CH.sub.3                                1539   2-C(═N--OCH.sub.3)--CH.sub.3                                                                  CH.sub.3 5-CH.sub.3                                1540   3-C(═N--OCH.sub.3)--CH.sub.3                                                                  CH.sub.3 5-CH.sub.3                                1541   4-C(═N--OCH.sub.3)--CH.sub.3                                                                  CH.sub.3 5-CH.sub.3                                ______________________________________                                    

The compounds of the formula I according to the invention are suitablefor controlling harmful fungi and animal pests of the insects, arachnidsand nematodes classes. They can be employed as fungicides and pesticidesin crop protection and in the hygiene, stored material protection andveterinary sectors.

The harmful insects include:

from the order of the butterflies (Lepidoptera), for example, Adoxophyesorana, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsiagemmatalis, Argyresthia conjugella, Autographa gamma, Cacoecia murinana,Capua reticulana, Choristoneura fumiferana, Chilo partellus,Choristoneura occidentalis, Cirphis unipuncta, Cnaphalocrocis medinalis,Crocidolomia binotalis, Cydia pomonella, Dendrolimus pini, Diaphanianitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpuslignosellus, Eupoecilia ambiguella, Feltia subterranea, Grapholithafunebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens,Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea,Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria,Laphygma exigua, Leucoptera scitella, Lithocolletis blancardella,Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantriamonacha, Lyonetia clerkella, Manduca sexta, Malacosoma neustria,Mamestra brassicae, Mocis repanda, Operophthera brumata, Orgyiapseudotsugata, Ostrinia nubilalis, Pandemis heparana, Panolis flammea,Pectinophora gossypiella, Phthorimaea operculella, Phyllocnistiscitrella, Pieris brassicae, Plathypena scabra, Platynota stultana,Plutella xylostella, Prays citri, Prays oleae, Prodenia sunia, Prodeniaornithogalli, Pseudoplusia includens, Rhyacionia frustrana,Scrobipalpula absoluta, Sesamia inferens, Sparganothis pilleriana,Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura,Syllepta derogata, Synanthedon myopaeformis, Thaumatopoea pityocampa,Tortrix viridana, Trichoplusia ni, Tryporyza incertulas, Zeirapheracanadensis, further Galleria mellonella and Sitotroga cerealella,Ephestia cautella, Tineola bisselliella;

from the order of the beetles (Coleoptera), for example, Agrioteslineatus, Agriotes obscurus, Anthonomus grandis, Anthonomus pomorum,Apion vorax, Atomaria linearis, Blastophagus piniperda, Cassidanebulosa, Cerotoma trifurcata, Ceuthorhynchus assimilis, Ceuthorhynchusnapi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi,Dendroctonus refipennis, Diabrotica longicornis, Diabrotica 12-punctata,Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis,Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis,Hypera postica, Ips typographus, Lema bilineata, Lema melanopus,Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrusoryzophilus, Melanotus communis, Meligethes aeneus, Melolonthahippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchussulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phylloperthahorticola, Phyllophaga sp., Phyllotreta chrysocephala, Phyllotretanemorum, Phyllotreta striolata, Popillia japonica, Psylliodes napi,Scolytus intricatus, Sitona lineatus, further Bruchus rufimanus, Bruchuspisorum, Bruchus lentis, Sitophilus granaria, Lasioderma serricorne,Oryzaephilus surinamensis, Rhyzopertha dominica, Sitophilus oryzae,Tribolium castaneum, Trogoderma granarium, Zabrotes subfasciatus;

from the order of the dipterous insects (Diptera), for example,Anastrepha ludens, Ceratitis capitata, Contarinia sorghicola, Dacuscucurbitae, Dacus oleae, Dasineura brassicae, Delia coarctata, Deliaradicum, Hydrellia griseola, Hylemyia platura, Liriomyza sativae,Liriomyza trifolii, Mayetiola destructor, Orseolia oryzae, Oscinellafrit, Pegomya hyoscyami, Phorbia antiqua, Phorbia brassicae, Phorbiacoarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tipula oleracea,Tipula paludosa, further Aedes aegypti, Aedes vexans, Anophelesmaculipennis, Chrysomya bezziana, Chrysomya hominivorax, Chrysomyamacellaria, Cordylobia anthropophaga, Culex pipiens, Fannia canicularis,Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans,Haplodiplosis equestris, Hypoderma lineata, Lucilia cuprina, Luciliasericata, Musca domestica, Muscina stabulans, Oestrus ovis, Tabanusbovinus, Simulium damnosum;

from the order of the thrips (Thysanoptera), for example, Frankliniellafusca, Frankliniella occidentalis, Frankliniella tritici, Haplothripstritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci;

from the order of the hymenopterous insects (Hymenoptera), for example,Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampaminuta, Hoplocampa testudinea, Iridomyrmes humilis, Iridomyrmexpurpureus, Monomorium pharaonis, Solenopsis geminata, Solenopsisinvicta, Solenopsis richteri;

from the order of the bugs (Heteroptera), for example, Acrosternumhilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus,Dysdercus intermedius, Eurygaster integriceps, Euschistusimpictiventris, Leptoglossus phyllopus, Lygus hesperus, Lyguslineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubeainsularis, Thyanta perditor;

from the order of the plant-sucking insects (Homoptera), for example,Acyrthosiphon onobrychis, Acyrthosiphon pisum, Adelges laricis,Aonidiella aurantii, Aphidula nasturtii, Aphis fabae, Aphis gossypii,Aphis pomi, Aulacorthum solani, Bemisia tabaci, Brachycaudus cardui,Brevicoryne brassicae, Dalbulus maidis, Dreyfusia nordmannianae,Dreyfusia piceae, Dysaphis radicola, Empoasca fabae, Eriosoma lanigerum,Laodelphax striatella, Macrosiphum avenae, Macrosiphum euphorbiae,Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzuspersicae, Myzus cerasi, Nephotettix cincticeps, Nilaparvata lugens,Perkinsiella saccharicida, Phorodon humuli, Planococcus citri, Psyllamali, Psylla piri, Psylla pyricol, Quadraspidiotus perniciosus,Rhopalosiphum maidis, Saissetia oleae, Schizaphis graminum, Selenaspidusarticulatus, Sitobion avenae, Sogatella furcifera, Toxoptera citricida,Trialeurodes abutilonea, Trialeurodes vaporariorum, Viteus vitifolii;

from the order of the termites (Isoptera), for example, Calotermesflavicollis, Leucotermes flavipes, Macrotermes subhyalinus, Odontotermesformosanus, Reticulitermes lucifugus, Termes natalensis;

from the order of the orthopterous insects (Orthoptera), for example,Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus,Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes,Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana,Schistocerca peregrina, Stauronotus maroccanus, Schistocerca gregaria,further Acheta domestica, Blatta orientalis, Blattella germanica,Periplaneta americana;

from the order of the Arachnoidea, for example, phytophagous mites suchas Aculops lycopersicae, Aculops pelekassi, Aculus schlechtendali,Brevipalpus phoenicis, Bryobia praetiosa, Eotetranychus carpini,Eutetranychus banksii, Eriophyes sheldoni, Oligonychus pratensis,Panonychus ulmi, Panonychus citri, Phyllocoptruta oleivora,Polyphagotarsonemus latus, Tarsonemus pallidus, Tetranychuscinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychusurticae, ticks such as Amblyomma americanum, Amblyomma variegatum, Argaspersicus, Boophilus annulatus, Boophilus decoloratus, Boophilusmicroplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus,Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Rhipicephalusappendiculatusand Rhipicephalus evertsias well as animal-parasitic mitessuch as Dermanyssus gallinae, Psoroptes ovisand Sarcoptes scabiei;

from the class of the nematodes, for example, root gall nematodes, eg.Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica,cyst-forming nematodes, eg. Globodera pallida, Globodera rostochiensis,Heterodera avenae, Heterodera glycines, Heterodera schachtii, migratoryendoparasites and semi-endoparasitic nematodes, eg. Heliocotylenchusmulticinctus, Hirschmanniella oryzae, Hoplolaimus spp, Pratylenchusbrachyurus, Pratylenchus fallax, Pratylenchus penetrans, Pratylenchusvulnus, Radopholus similis, Rotylenchus reniformis, Scutellonema bradys,Tylenchulus semipenetrans, stem and leaf nematodes eg. Anguina tritici,Aphelenchoides besseyi, Ditylenchus angustus, Ditylenchus dipsaci, virusvectors, eg. Longidorus spp., Trichodorus christei, Trichodorusviruliferus, Xiphinema index, Xiphinema mediterraneum.

The compounds I can be applied as such, in the form of theirformulations or the application forms prepared therefrom, eg. in theform of directly sprayable solutions, powders, suspensions ordispersions, emulsions, oil dispersions, pastes, dust compositions,scattering compositions or granules, by spraying, atomizing, dusting,scattering or watering. The application forms depend entirely on theintended uses; in each case they should if possible guarantee the finestdispersion of the active compounds according to the invention.

The compounds of the formula I are in some cases systemically active asfungicides. They can be employed as foliar and soil fungicides against abroad spectrum of phytopathogenic fungi, in particular from theAscomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes classes.

They are of particular importance for controlling a multiplicity offungi on various crop plants such as wheat, rye, barley, oats, rice,corn, grass, cotton, soybeans, coffee, sugar cane, grapes, fruit anddecorative plants and vegetable plants such as cucumbers, beans andcucurbits, and on the seeds of these plants.

The compounds I are specifically suitable for controlling the followingplant diseases:

Erysiphe graminis(powdery mildew) in cereals,

Erysiphe cichoracearumand Sphaerotheca fuligineaon cucurbits,

Podosphaera leucotrichaon apples,

Uncinula necatoron vines,

Pucciniaspecies on cereals,

Rhizoctoniaspecies on cotton and grass,

Ustilago species on cereals and sugar cane,

Venturia inaequalis(scab) on apples,

Helminthosporiumspecies on cereals,

Septoria nodorumon wheat,

Botrytis cinerea(gray mold) on strawberries, vines,

Cercospora arachidicolaon groundnuts,

Pseudocercosporella herpotrichoideson wheat, barley,

Pyricularia oryzaeon rice,

Phytophthora infestanson potatoes and tomatoes,

Fusariumand Verticilliumspecies on various plants,

Plasmopara viticolaon vines,

Alternariaspecies on vegetables and fruit.

The novel compounds can also be employed in the protection of materials,eg. for the protection of wood, paper and textiles eg. againstPaecilomyces variotii.

They can be converted into the customary formulations, such assolutions, emulsions, suspensions, dusts, powders, pastes or granules.The use forms here depend on the particular intended use; in each casethey should if possible guarantee the finest dispersion of the activecompounds.

The formulations are prepared in a known manner, eg. by extending theactive compound with solvents and/or carriers, if desired usingemulsifiers and dispersants, where if water is used as a diluent otherorganic solvents can also be used as auxiliary solvents.

Suitable auxiliaries for this purpose are mainly:

solvents such as aromatics (eg. xylene), chlorinated aromatics (eg.chlorobenzenes), paraffins (eg. petroleum fractions), alcohols (eg.-methanol, butanol), ketones (eg. cyclohexanone), amines (eg.ethanolamine, dimethylformamide) and water;

carriers such as ground natural minerals (eg. kaolins, argil-laceousearths, talc, chalk) and ground synthetic minerals (eg. highly dispersesilica, silicates);

emulsifiers such as nonionic and anionic emulsifiers (eg.polyoxyethylene fatty alcohol ethers, alkylsulfonates andarylsulfonates) and

dispersants such as lignin-sulfite waste liquors and methyl-cellulose.

Suitable surface-active substances are the alkali metal, alkaline earthmetal and ammonium salts of aromatic sulfonic acids, eg. lignosulfonic,phenolsulfonic, naphthalenesulfonic and dibutylnaphthalenesulfonic acid,and also of fatty acids, alkyl-and alkylarylsulfonates, alkyl, laurylether and fatty alcohol sulfates, as well as salts of sulfated hexa-,hepta- and octadecanols, and also of fatty alcohol glycol ethers,condensation products of sulfonated naphthalene and its derivatives withformaldehyde, condensation products of naphthalene or of thenaphthalenesulfonic acids with phenol and formaldehyde, polyoxyethyleneoctylphenyl ether, ethoxylated isooctyl-, octyl- or nonylphenol,alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyetheralcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkylethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignin-sulfite waste liquors or methylcellulose.

Aqueous use forms can be prepared from emulsion concentrates,dispersions, pastes, wettable powders or water-dispersible granules byaddition of water. To prepare emulsions, pastes or oil dispersions, thesubstrates can be homogenized in water as such or dissolved in an oil orsolvent, by means of wetting agents, adhesives, dispersants oremulsifiers. However, concentrates consisting of active substance,wetting agent, adhesive, dispersant or emulsifier and possibly solventor oil can also be prepared which are suitable for dilution with water.

Powder, broadcasting and dusting compositions can be prepared by mixingor joint grinding of the active substances with a solid carrier.

Granules, eg. coated, impregnated and homogeneous granules, can beprepared by binding the active compounds to solid carriers.

Solid carriers are mineral earths such as silicic acids, silica gels,silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay,dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers, such asammonium sulfate, ammonium phosphate, ammonium nitrate, ureas andvegetable products, such as cereal flour, tree bark meal, wood meal andnutshell meal, cellulose powder or other solid carriers. The activecompound concentrations in the ready-to-use preparations can be variedwithin relatively wide ranges.

Very generally, the compositions contain from 0.0001 to 95% by weight ofactive compound.

Formulations containing more than 95% by weight of active compound canbe applied highly successfully in the ultra-low volume process (ULV), iteven being possible to use the active compound without additives.

For use as fungicides, concentrations of from 0.01 to 95% by weight,preferably of from 0.5 to 90% by weight, of active compound arerecommended. For use as insecticides, formulations containing from0.0001 to 10% by weight, preferably from 0.01 to 1% by weight, of activecompound are suitable.

The active compounds are normally employed in a purity of from 90% to100%, preferably from 95% to 100% (according to NMR spectrum).

EXAMPLES OF SUCH PREPARATIONS ARE

I. a solution of 90 parts by weight of a compound I according to theinvention and 10 parts by weight of N-methyl-α-pyrrolidone, which issuitable for application in the form of very small drops;

II. a solution of 20 parts by weight of a compound I according to theinvention in a mixture of 80 parts by weight of alkylated benzene, 10parts by weight of the addition product of from 8 to 10 mol of ethyleneoxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight ofcalcium salt of dodecylbenzenesulfonic acid, 5 parts by weight of theaddition product of 40 mol of ethylene oxide to 1 mol of castor oil; adispersion is obtained by finely dispersing the formulation in water.

III. a solution of 20 parts by weight of a compound I according to theinvention in a mixture of 40 parts by weight of cyclohexanone, 30 partsby weight of iso-butanol, 20 parts by weight of the addition product of7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts byweight of the addition product of 40 mol of ethylene oxide to 1 mol ofcastor oil; a dispersion is obtained by finely dispersing theformulation in water.

IV. an aqueous dispersion of 20 parts by weight of a compound Iaccording to the invention in a mixture of 25 parts by weight ofcyclohexanone, 65 parts by weight of a mineral oil fraction of boilingpoint from 210 to 280° C. and 10 parts by weight of the addition productof 40 mol of ethylene oxide to 1 mol of castor oil; a dispersion isobtained by finely dispersing the formulation in water.

V. a mixture, ground in a hammer mill, of 20 parts by weight of acompound I according to the invention, 3 parts by weight of the sodiumsalt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of thesodium salt of a lignosulfonic acid from a sulfite waste liquor and 60parts by weight of powdered silica gel; a spray mixture is obtained byfinely dispersing the mixture in water;

VI. an intimate mixture of 3 parts by weight of a compound I accordingto the invention and 97 parts by weight of finely divided kaolin; thisdusting composition contains 3% by weight of active compound;

VII. an intimate mixture of 30 parts by weight of a compound I accordingto the invention, 92 parts by weight of powdered silica gel and 8 partsby weight of liquid paraffin which has been sprayed onto the surface ofthis silica gel; this preparation gives the active compound a goodadherence;

VIII. a stable aqueous dispersion of 40 parts by weight of a compound Iaccording to the invention, 10 parts by weight of the sodium salt of aphenolsulfonic acid/urea/formal-dehyde condensate, 2 parts by weight ofsilica gel and 48 parts by weight of water, which can be furtherdiluted;

IX. a stable oily dispersion of 20 parts by weight of a compound Iaccording to the invention, 2 parts by weight of the calcium salt ofdodecylbenzenesulfonic acid, 8 parts by weight of fatty alcoholpolyglycol ether, 2 parts by weight of the sodium salt of aphenolsulfonic acid/urea/formaldehyde condensate and 68 parts by weightof a paraffinic mineral oil;

X. a mixture, ground in a hammer mill, of 10 parts by weight of acompound I according to the invention, 4 parts by weight of the sodiumsalt of diisobutylnaphthalene-α-sulfonic acid, 20 parts by weight of thesodium salt of a lignosulfonic acid from a sulfite waste liquor, 38parts by weight of silica gel and 38 parts by weight of kaolin. Byfinely dispersing the mixture in 10,000 parts by weight of water, aspray mixture is obtained which contains 0.1% by weight of the activecompound.

The compounds I are applied by treating the fungi or the seed, plants,materials or the soil to be protected from fungal attack with afungicidally active amount of the active compounds.

They are applied before or after the infection of the materials, plantsor seed by the fungi.

Depending on the type of effect desired, the application rates are from0.02 to 3 kg of active compound per ha, preferably from 0.1 to 1 kg/ha.

In seed treatment, amounts of active compound of from 0.001 to 50 g,preferably from 0.01 to 10 g, per kilogram of seed are in generalneeded.

The application rate of active compound for controlling pests underoutdoor conditions is from 0.02 to 10, preferably from 0.1 to 2.0 kg/haof active compound.

The compounds I, on their own or in combination with herbicides orfungicides, can also be applied jointly mixed with further cropprotection agents, for example with growth regulators or with agents forcontrolling pests or bacteria. Of interest is also the miscibility withfertilizers or with mineral salt solutions which are employed foreliminating nutritional and trace element deficiencies.

The crop protection agents and fertilizers can be added to thecompositions according to the invention in a weight ratio of from 1:10to 10:1, if appropriate even only immediately before use (tank mix). Onmixing with fungicides or insecticides, in many cases an increase in thefungicidal spectrum of action is obtained here.

The following list of fungicides with which the compounds according tothe invention can be applied jointly is intended to illustrate thecombination possibilities, but not to restrict them:

sulfur, dithiocarbamates and their derivatives, such as ferricdimethyldithiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate,manganese zinc ethylenediamine bisdithiocarbamate, tetramethylthiuramdisulfide, ammonia complex of zinc N,N-ethylenebisdithiocarbamate,ammonia complex of zinc N,N'-propylenebisdithiocarbamate, zincN,N'-propylenebisdithiocarbamate, N,N'-polypropylenebis(thiocarbamoyl)disulfide; nitro derivatives, such as dinitro(1-methylheptyl)phenylcrotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate,2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate, diisopropyl5-nitroisophthalate;

heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate,2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethylphthalimidophosphonothioate, 5-amino-1-β- bis(dimethylamino)-phosphinyl!-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone,2-thio-1,3-dithiolo-β- 4,5-b!quinoxaline, methyl1-(butylcarbamoyl)-2-benzimidazolecarbamate,2-methoxycarbonylaminobenzimidazole, 2-(fur-2-yl)benzimidazole,2-(thiazol-4-yl)-benzimidazole,N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide,N-trichloro-methylthiotetrahydrophthalimide,N-trichloro-methylthiophthalimide,N-dichlorofluoro-methylthio-N-',N'-dimethyl-N-phenylsulfamide,5-ethoxy-3-trichloro-methyl-1,2,3-thiadiazole,2-thiocyanato-methylthiobenzothiazole,1,4-dichloro-2,5-dimethoxybenzene,4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, 2-thiopyridine1-oxide, 8-hydroxyquinoline or its copper salt,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide,2,5-dimethylfuran-3-carboxanilide,2,4,5-tri-methylfuran-3-carboxanilide,N-cyclohexyl-2,5-dimethylfuran-3-carboxamide,N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide,2-methylbenzanilide, 2-iodobenzanilide,N-formyl-N-morpholine-2,2,2-trichloroethyl acetal,piperazine-1,4-diylbis 1(2,2,2-trichloroethyl))formamide,1-(3,4-dichloroanilino)(1-formylamino-2,2,2-trichloroethane,2,6-dimethyl-N-tridecylmorpholine or its salts,2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-3-(p-tert-butylphenyl)-2-methylpropyl!-cis-2,6-dimethylmor-pholine, N-3-(p-tert-butylphenyl)-2-methylpropyl!piperidine, 1-2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl!-1H-1,2,4-triazole,1-2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl!-1H-1,2,4-triazole,N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolylurea,1-(4-chlorophenoxy)-3,3-dimethyl 1-(1H-1,2,4-triazol 1-yl)-2-butanone,1-(4-chlorophenoxy)-3,3-dimethyl 1-(1H-1,2,4-triazol 1-yl)-2-butanol,α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidine-methanol,5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine,bis(p-chlorophenyl)-3-pyridine-methanol,1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene,1,2-bis(3-methoxycarbonyl-2-thioureido)benzene,

and also various fungicides, such as dodecylguanidine acetate, 3-3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl!glutarimide,hexachlorobenzene, DL-methyl-N-(2,6-dimethylphenyl)-N-2-furoylalaninate, DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)alanine methylester, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone,DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester,5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,3-(3,5-dichlorophenyl)-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione,3-(3,5-dichlorophenyl)-l-isopropylcarbamoylhydantoin,N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,2-cyano- N-ethylaminocarbonyl-2-methoximino !-acetamide, 1-2-(2,4-dichlorophenyl)pentyl!-1H-1,2,4-triazole,2,4-difluoro-α-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol,N-(3-chloro-2,6-dinitro-4-trifluoro-methylphenyl)-5-trifluoro-methyl-3-chloro-2-aminopyridine,1-((bis(4-fluorophenyl)-methylsilyl)-methyl)-1H-1,2,4-triazole.

Synthesis examples

The procedures described in the synthesis examples below were used withappropriate modification of the starting compounds to obtain furthercompounds I. The compounds thus obtained are listed with physical datain the following table.

1. MethylN-methoxy-N-(2-(4'-(2''-fluorophenyl)-2'-methoxyphe-noxymethyl)phenyl)carbamate##STR11##

A mixture of 1 g (2.6 mmol) of -methylN-methoxy-N-(2-(4'-bromo-2'-methylphenoxymethyl)phenyl)carbamate(preparation in the same way as in WO 93/15046), 0.55 g (3.9 mmol) of2-fluorophenylboronic acid and 0.33 g (3.9 mmol) of NaHCO₃ is refluxedand stirred in 4 ml of dimethoxyethane/water 1:1 for about 5 hours. Thereaction mixture is then cooled and diluted with water, and the aqueousphase is extracted three times with -methylene chloride. The combinedorganic phases are extracted with water, dried over MgSO₄ andconcentrated. The residue obtained is 1 g (95%) of the title compound aspale yellow crystals (m.p. =71° C.).

¹ H-NMR (CDCl₃ ; δ in ppm): 7.7(d,1H,phenyl); 7.35(m,8H,phenyl);6.95(m,2H,phenyl); 5.2(s,2H,OCH₂); 3.82(s,3H,OCH₃); 3.75(s,3H,OCH₃);2.4(s,3H,CH₃)

                  TABLE B                                                         ______________________________________                                        Physical data of some compounds                                               No.  R.sub.m R.sup.2 R.sub.n.sup.1                                                                      M.p. °C.! or NMR (CDCl.sub.3 ; δ                                 in ppm)                                             ______________________________________                                        1    4-F     F       H    3.8(s, 3H); 3.73(s, 3H)                             2    2-F     CH.sub.3                                                                              H    71                                                  3    3-OCH.sub.3                                                                           CH.sub.3                                                                              H    3.85(s, 3H); 3.8(s, 3H); 3.73(s, 3H)                4    2-CH.sub.3                                                                            CH.sub.3                                                                              H    3.8(s, 3H); 3.73(s, 3H)                             5    2,4-Cl.sub.2                                                                          CH.sub.3                                                                              H    3.82(s, 3H); 3.75(s, 3H)                            6    4-OCH.sub.3                                                                           CH.sub.3                                                                              H    113                                                 7    2-OCH.sub.3                                                                           CH.sub.3                                                                              H    3.8(2s, each 3H); 3.75(s, 3H)                       8    3,4-Cl.sub.2                                                                          CH.sub.3                                                                              H    3.8(s, 3H); 3.73(s, 3H)                             9    3,5-Cl.sub.2                                                                          CH.sub.3                                                                              H    3.83(s, 3H); 3.77(s, 3H)                            10   4-CH.sub.3                                                                            CH.sub.3                                                                              H    3.7(s, 3H); 3.66(s, 3H) (in DMSO-d.sub.6)           ______________________________________                                    

Examples of the action against harmful fungi

It was possible to show the fungicidal action of the compounds of theformula I by the following tests:

The active compounds were prepared as a 20% strength emulsion in amixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN(Lutensol® AP6, wetting agent having emulsifier and dispersant actionbased on ethoxylated alkylphenols) and 10% by weight of Emulphor® EL(Emulan® EL, emulsifier based on ethoxylated fatty alcohols) and dilutedwith water according to the concentration desired.

Activity against Plasmopara viticola

Potted vines (variety: Muller Thurgau) were sprayed with the activecompound preparation until dripping wet. After 8 days, the plants weresprayed with a zoospore suspension of the fungus Plasmopara viticola andkept at high atmospheric humidity for 5 days at 20°-30° C. Beforeassessment, the plants were then kept at high atmospheric humidity for16 h. Assessment was carried out visually.

In this test, the plants treated with the active compounds 2, 3, 4, 5,6, 7, 9 and 10 according to the invention showed a fungal attack of 5%or less, while the untreated plants (control test) were attacked to 70%.

Activity against Puccinia recondita (brown rust of wheat)

Leaves of wheat seedlings (Kanzler variety) were dusted with spores ofbrown rust (Puccinia recondita). The plants treated in this way wereincubated for 24 h at 20°-22° C. and a relative atmospheric humidity of90-95% and then treated with the aqueous active compound preparation.After a further 8 days at 20°-22° C. and 65-70% relative atmospherichumidity, the extent of the fungal development was determined.Assessment was carried out visually. In this test, the plants treatedwith the active compounds 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10 according tothe invention showed a fungal attack of 5% or less, while the untreatedplants (control test) were attacked to 65%.

Examples of the action against animal pests

It was possible to show the action of the compounds of the generalformula I against animal pests by the following tests:

The active compounds were prepared

a) as a 0.1% strength solution in acetone or

b) as a 10% strength emulsion in a mixture of 70% by weight ofcyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wettingagent having emulsifier and dispersant action based on ethoxylatedalkylphenols) and 10% by weight of Emulphor®EL (Emulan® EL, emulsifierbased on ethoxylated fatty alcohols)

and diluted with acetone in the case of a) or with water in the case ofb) according to the desired concentration.

After conclusion of the tests, the lowest concentration at which thecompounds still caused an 80-100% inhibition or mortality in comparisonwith untreated control tests was determined in each case (activitythreshold or minimum concentration).

We claim:
 1. A 2- 4-biphenyloxymethylene!anilide of the formula I##STR12## where the indices and the substituents have the followingmeanings: R is cyano, nitro, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl,C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-haloalkylthio, C₁ -C₄ -alkylamino, di-C₁ -C₄ -alkylamino, C₁ -C₄-alkylcarbonyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylaminocarbonyl,di(C₁ -C₄ -alkyl)aminocarbonyl, C₁ -C₄ -alkylcarbonylamino, C₁ -C₄-alkylcarbonyl(C₁ -C₄ -alkylamino), C₂ -C₄ -alkenyl, C₃ -C₄ -alkenyloxy,C₂ -C₄ -alkynyl, C₃ -C₄ -alkynyloxy, C₃ -C₆ -cycloalkyl orC(R^(a))═NOR^(b) ;R^(a) and R^(b) are hydrogen, alkyl, alkenyl, alkynyl,cycloalkyl or cycloalkenyl; m is 1, 2, 3, 4 or 5, it being possible forthe radicals R to be different if m is greater than 1; R¹ is cyano,nitro, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄-alkylamino, di-C₁ -C₄ -alkylamino, C₁ -C₄ -alkylcarbonyl, C₁ -C₄-alkoxycarbonyl, C₁ -C₄ -alkylaminocarbonyl, di(C₁ -C₄-alkyl)aminocarbonyl, C₁ -C₄ -alkylcarbonylamino, C₁ -C₄-alkylcarbonyl(C₁ -C₄ -alkylamino), C₂ -C₄ -alkenyl, C₃ -C₄ -alkenyloxy,C₂ -C₄ -alkynyl, C₃ -C₄ -alkynyloxy, C₃ -C₆ -cycloalkyl orC(R^(a))═NOR^(b) ; n is 0, 1 or 2, it being possible for the radicals R¹to be different if n is 2; R² is cyano, nitro, halogen, C₁ -C₄ -alkyl,C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄-alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkylamino, di-C₁ -C₄-alkylamino, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄-alkylaminocarbonyl, di(C₁ -C₄ -alkyl)aminocarbonyl, C₁ -C₄-alkylcarbonylamino, C₁ -C₄ -alkylcarbonyl(C₁ -C₄ -alkylamino), C₂ -C₄-alkenyl, C₃ -C₄ -alkenyloxy, C₂ -C₄ -alkynyl, C₃ -C₄ -alkynyloxy, C₃-C₆ -cycloalkyl or C(R^(a))═NOR^(b) ; R³ is nitro, cyano,halogen,unsubst. or subst. alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy,alkynyloxy or C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄-alkylaminocarbonyl, di(C₁ -C₄ -alkyl)aminocarbonyl, C₁ -C₄-alkylcarbonylamino, C₁ -C₄ -alkylcarbonyl(C₁ -C₄ -alkylamino),C(R^(a))═NOR^(b) or in the case where o is greater than 1, is additionalan unsubst. or subst. bridge bonded to two adjacent ring atoms, whichcan carry three to four members from the group consisting of 3 or 4carbon atoms, and 2 or 3 carbon atoms and 1 or 2 nitrogen, oxygen and/orsulfur atoms, it being possible for this bridge, together with the ringto which it is bonded, to form a partially unsaturated or aromaticradical; o is 0, 1, 2, 3 or 4, it being possible for the substituents R³to be different if n is greater than 1; R⁴ is hydrogen,unsubst. orsubst. alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkylcarbonylor alkoxycarbonyl; X is a direct bond or CH₂, O or NR^(c) ; R^(c) ishydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl; R⁵ isalkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, oror in the casewhere X is NR^(c), is additionally hydrogen.
 2. A process for preparingthe compounds of the formula I as claimed in claim 1, where R⁴ ishydrogen and X is a direct bond or oxygen, which comprises converting abenzyl derivative of the formula II ##STR13## where L¹ is anucleophilically replaceable group, ##STR14## into the corresponding 2-4-biphenyloxymethylene!nitrobenzene of the formula IV ##STR15## in thepresence of a base using a 4-biphenol of the formula III, then reducingIV to the N-hydroxyaniline of the formula Va ##STR16## and converting Vainto I using a carbonyl compound of the formula VI

    L.sup.2 --CO--X--R.sup.5                                   VI

where L² is halogen.
 3. A process for preparing the compounds of theformula I as claimed in claim 1, where R⁴ is not hydrogen, whichcomprises reducing a benzyl derivative of the formula IIa ##STR17##first to the corresponding N-hydroxyaniline of the formula Vb ##STR18##converting Vb into the corresponding anilide of the formula VII##STR19## using a carbonyl compound of the formula VI as set forth inclaim 2 and then converting VII using a compound VIII

    L.sup.3 --R.sup.4                                          VIII

where L³ is a nucleophilically replaceable group and R⁴ is not hydrogen,into the amide of the formula IX ##STR20## then converting IX into thecorresponding benzyl halide of the formula X ##STR21## where Hal is ahalogen atom, and converting X into I in the presence of a base using a4-biphenol of the formula III as set forth in claim
 2. 4. A process forpreparing the compounds I as claimed in claim 1, where R⁴ is nothydrogen, which comprises reacting a corresponding compound of theformula I where R⁴ is hydrogen with an appropriate compound of theformula VIII as set forth in claim
 3. 5. A process for preparing thecompounds of the formula I where X is NR^(c), which comprises convertinga benzanilide of the formula IXa ##STR22## where A is alkyl or phenyl,into the corresponding benzyl halide of the formula Xa ##STR23## whereHal is a halogen atom, converting Xa into a compound of the formula I.A##STR24## in the presence of a base using a 4-biphenol of the formulaIII as set forth in claim 2 and then reacting I.A with an amine of theformula XIa or XIb

    H.sub.2 NR.sup.c                                           XIa

    HNR.sup.c R.sup.5                                          XIb

to give I.
 6. A process for preparing compounds of the formula I.A asset forth in claim 5, where A is phenyl, which comprises converting anN-hydroxyaniline of the formula VA as set forth in claim 2 using aphenyl carbonate of the formula VIA

    L.sup.2 --CO.sub.2 --C.sub.6 H.sub.5                       VIA

where L² is a halogen atom, into the corresponding N-hydroxycarbamate ofthe formula IB ##STR25## and then reacting IB with a compound VIII asset forth in claim 3 to give I.A.
 7. A process for preparing thecompound I as claimed in claim 1, which comprises reacting a compound ofthe formula XIV ##STR26## where Hal is a halogen atom, with anorganometallic compound of the formula XV ##STR27## where L-M is ametal-containing radical, in the presence of a palladium catalyst.
 8. Anintermediate of the formula XII ##STR28## where Y is NO₂, NHOH, NHOR⁴,N(OH)--CO₂ C₆ H₅ or N(OR⁴)--CO₂ C₆ H₅ and the indices m, n and o and thesubstituents R, R¹, R², R³ and R⁴ have the meanings given in claim
 1. 9.A composition suitable for controlling animal pests or harmful fungi,containing a solid or liquid carrier and a compound of the generalformula I as claimed in claim
 1. 10. The use of the compounds I asclaimed in claim 1 for preparing a composition suitable for controllinganimal pests or harmful fungi.
 11. A method of controlling animal pestsor harmful fungi, which comprises treating the pests or fungi to becontrolled or the materials, plants, soil or seed to be protected fromthem with an effective amount of a compound of the general formula I asclaimed in claim
 1. 12. The 2- 4-biphenyloxymethylene!anilide of theformula I as set forth in claim 1, whereinR_(m) is 2,4-dichloro; n is 0;R² is methyl; o is 0; R⁴ and R⁵ are methyl, and X is oxygen.